Glufosinate formulations containing amines or ammonium salts

ABSTRACT

The invention relates to a liquid herbicidal composition comprising a) glufosinate, or a salt thereof, an amine component; and a compound of formula (I) [R-(A)x-OSO3−]-M+ (I); wherein al variables have a meaning as defined herein. It also relates to a method for increasing the herbicidal activity of liquid herbicidal compositions comprising glufosinate or a salt thereof, and a compound of formula (I) comprising the step of contacting the liquid herbicidal composition with the amine component; and to a method for treating plant propagation material comprising the step of treating plant propagation material with the herbicidal composition.

The invention relates to a liquid herbicidal composition comprising a)glufosinate, or a salt thereof; b) an amine component selected fromprimary, secondary, tertiary amines, and ammonium salts thereof, andquaternary ammonium salts; wherein the molecular weight of the primary,secondary or tertiary amines, of the ammonium cation in the ammoniumsalts, or of the quaternary ammonium cation in the quaternary ammoniumsalts is from 32 to 200 g/mol; and c) a compound of formula (I)

[R-(A)_(x)-OSO₃ ⁻]-M⁺  (I);

wherein the variables have a meaning as defined herein below.

Further objects are a method for controlling undesirable vegetation,which method comprises applying the herbicidal composition to a locuswhere undesirable vegetation is present or is expected to be present;the use of the amine component for increasing the herbicidal activity ofliquid herbicidal compositions comprising glufosinate, or a saltthereof, and a compound of formula (I); a method for increasing theherbicidal activity of liquid herbicidal compositions comprisingglufosinate or a salt thereof, and a compound of formula (I) comprisingthe step of contacting the liquid herbicidal composition with the aminecomponent; a method of producing the herbicidal composition comprisingthe step of contacting the amine component with the compound of formula(I) and glufosinate or a salt thereof in any given order; plantpropagation material comprising the herbicidal composition; and to amethod for treating plant propagation material comprising the step oftreating plant propagation material with the herbicidal composition.

There is an ongoing need to find additives for agrochemical compositionsthat enhance the biological effectivity of the composition, increase itsphysical and/or chemical stability, or increase the loading of theagrochemical composition with active ingredients and/or adjuvants.Increased biological effectivity allows for lower application rates ofthe active ingredient, which reduces costs and health risks for theapplicant. Higher loading of agrochemical compositions reduces theweight of a given packaging unit, thereby facilitating transportationand handling of the canisters containing the agrochemical compositions.However, agrochemical compositions with higher loading of agrochemicalactive ingredients and/or adjuvants suffer from stability problems, suchas gelling, flocculation, and creaming. Also agrochemical compositionswith higher loading often have a high viscosity, which negativelyaffects their handling by the applicant.

U.S. Pat. No. 10,091,994B2 discloses additives for agrochemicalcompositions. The additives are alkoxylated and sulfonated alcohols,which are present in the form of salts and wherein the cation may besodium.

It was the objective of the present invention to provide herbicidalcompositions of glufosinate or its salts that have an increasedbiological effect, in particular an increased herbicidal effect againstundesired vegetation, have an enhanced physical and/or chemicalstability, high loading with agrochemical active ingredients and/oradjuvants and at the same can be easily handled by the applicant.

It was surprisingly found that the amine component increases thebiological activity of liquid herbicidal compositions comprisingglufosinate. The improved biological activity relates both the increasedherbicidal effect against unwanted vegetation, to a reduced damage ofcertain crop plants, and an enhanced defoliation effect. Furtheradvantages are that the herbicidal compositions have a high loading withglufosinate, that they are physically stable upon storage.

Accordingly, the invention relates to a liquid herbicidal compositioncomprising

-   -   a) glufosinate, or a salt thereof;    -   b) an amine component selected from primary, secondary, tertiary        amines, and ammonium salts thereof, and quaternary ammonium        salts;    -   wherein the molecular weight of the primary, secondary or        tertiary amines, of the ammonium cation in the ammonium salts,        or of the quaternary ammonium cation in the quaternary ammonium        salts is from 32 to 200 g/mol;    -   c) a compound of formula (I)

[R-(A)_(x)-OSO₃ ⁻]-M⁺  (I);

wherein

-   -   R is C₁₀-C₁₆-alkyl, C₁₀-C₁₆-alkenyl, or C₁₀-C₁₆-alkynyl;    -   each A is independently a group

wherein

-   -   R^(A), R^(B), R^(C), and R^(D) are independently H, CH₃, or        CH₂CH₃ with the proviso that the sum of C-atoms of R^(A), R^(B),        R^(C), and R^(D) is up to 2;    -   M⁺ is a monovalent cation; and    -   the index x is a number from 1 to 10.

The terms compounds of formula (I) and compound of formula (I) as usedherein have the same meaning and refer to a situation in which at leastone compound of formula (I) is present. In general, terms mentioned intheir plural form refer to a situation wherein only the singular termapplies as well unless specifically expressed otherwise.

The organic moieties groups mentioned in the above definitions of thevariables are—like the term halogen—collective terms for individuallistings of the individual group members. The prefix C_(n)-C_(m)indicates in each case the possible number of carbon atoms in the group.

The term “substituted with”, e.g. as used in “partially, or fullysubstituted with” means that one or more, e.g. 1, 2, 3, 4 or 5 or all ofthe hydrogen atoms of a given radical have been replaced by one or more,same or different substituents. Accordingly, for substituted cyclicmoieties, e.g. 1-cyanocyclopropyl, one or more of the hydrogen atoms ofthe cyclic moiety may be replaced by one or more, same or differentsubstituents.

The term “C_(n)-C_(m)-alkyl” as used herein (and also inC_(n)-C_(m)-alkylamino, di-C_(n)-C_(m)-alkylamino,C_(n)-C_(m)-alkylaminocarbonyl, di-(C_(n)-C_(m)-alkylamino)carbonyl)refers to a branched or unbranched saturated hydrocarbon group having nto m, e.g. 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, forexample methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl,2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl,3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl,1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl,3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl,1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl,3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl,1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl,heptyl, octyl, 2-ethylhexyl, nonyl and decyl and their isomers.C₁-C₄-alkyl means for example methyl, ethyl, propyl, 1-methylethyl,butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl.

The term “C₂-C_(m)-alkenyl” as used herein intends a branched orunbranched unsaturated hydrocarbon group having 2 to m, e.g. 2 to 10 or2 to 6 carbon atoms and a double bond in any position, such as ethenyl,1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl,3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl,1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl,3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl,3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl,3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl,3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl,1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl,1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl,1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl,4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl,3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl,2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl,1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl,4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl,1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl,2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl.

The term “C₂-C_(m)-alkynyl” as used herein refers to a branched orunbranched unsaturated hydrocarbon group having 2 to m, e.g. 2 to 10 or2 to 6 carbon atoms and containing at least one triple bond, such asethynyl, propynyl, 1-butynyl, 2-butynyl, and the like.

Similarly, “C_(n)-C_(m)-alkoxy” refers to straight-chain or branchedalkyl groups having n to m carbon atoms, e.g. 1 to 10, in particular 1to 6 or 1 to 4 carbon atoms (as mentioned above) bonded through oxygenat any bond in the alkyl group. Examples include C₁-C₄-alkoxy such asmethoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy andtert-butoxy.

The term “hetaryl” or “aromatic heterocycle” or “aromatic heterocyclicring” includes monocyclic 5- or 6-membered heteroaromatic radicalscomprising as ring members 1, 2, 3 or 4 heteroatoms selected from N, Oand S. Examples of 5- or 6-membered heteroaromatic radicals includepyridyl, i.e. 2-, 3-, or 4-pyridyl, pyrimidinyl, i.e. 2-, 4- or5-pyrimidinyl, pyrazinyl, pyridazinyl, i.e. 3- or 4-pyridazinyl,thienyl, i.e. 2- or 3-thienyl, furyl, i.e. 2- or 3-furyl, pyrrolyl, i.e.2- or 3-pyrrolyl, oxazolyl, i.e. 2-, 3- or 5-oxazolyl, isoxazolyl, i.e.3-, 4- or 5-isoxazolyl, thiazolyl, i.e. 2-, 3- or 5-thiazolyl,isothiazolyl, i.e. 3-, 4- or 5-isothiazolyl, pyrazolyl, i.e. 1-, 3-, 4-or 5-pyrazolyl, i.e. 1-, 2-, 4- or 5-imidazolyl, oxadiazolyl, e.g. 2- or5-[1,3,4]oxadiazolyl, 4- or 5-(1,2,3-oxadiazol)yl, 3- or5-(1,2,4-oxadiazol)yl, 2- or 5-(1,3,4-thiadiazol)yl, thiadiazolyl, e.g.2- or 5-(1,3,4-thiadiazol)yl, 4- or 5-(1,2,3-thiadiazol)yl, 3- or5-(1,2,4-thiadiazol)yl, triazolyl, e.g. 1H-, 2H- or3H-1,2,3-triazol-4-yl, 2H-triazol-3-yl, 1H-, 2H-, or 4H-1,2,4-triazolyland tetrazolyl, i.e. 1H- or 2H-tetrazolyl.

The terms “heterocycle”, “heterocyclyl” or “heterocyclic ring” includes,unless otherwise indicated, in general 5- or 6-membered, in particular6-membered monocyclic heterocyclic radicals. The heterocyclic radicalsmay be saturated, partially unsaturated, or fully unsaturated. As usedin this context, the term “fully unsaturated” also includes “aromatic”.In a preferred embodiment, a fully unsaturated heterocycle is thus anaromatic heterocycle, preferably a 5- or 6-membered aromatic heterocyclecomprising one or more, e.g. 1, 2, 3, or 4, preferably 1, 2, or 3heteroatoms selected from N, O and S as ring members. Examples ofaromatic heterocycles are provided above in connection with thedefinition of “hetaryl”. Unless otherwise indicated, “hetaryls” are thuscovered by the term “heterocycles”. The heterocyclic non-aromaticradicals usually comprise 1, 2, 3, 4 or 5, preferably 1, 2 or 3heteroatoms selected from N, O and S as ring members, where S-atoms asring members may be present as S, SO or SO₂. Examples of 5- or6-membered heterocyclic radicals comprise saturated or unsaturated,non-aromatic heterocyclic rings, such as oxiranyl, oxetanyl, thietanyl,thietanyl-S-oxid (S-oxothietanyl), thietanyl-S-dioxid(S-dioxothiethanyl), pyrrolidinyl, pyrrolinyl, pyrazolinyl,tetrahydrofuranyl, dihydrofuranyl, 1,3-dioxolanyl, thiolanyl,S-oxothiolanyl, S-dioxothiolanyl, dihydrothienyl, S-oxodihydrothienyl,S-dioxodihydrothienyl, oxazolidinyl, oxazolinyl, thiazolinyl,oxathiolanyl, piperidinyl, piperazinyl, pyranyl, dihydropyranyl,tetrahydropyranyl, 1,3- and 1,4-dioxanyl, thiopyranyl, S.oxothiopyranyl,S-dioxothiopyranyl, dihydrothiopyranyl, S-oxodihydrothiopyranyl,S-dioxodihydrothiopyranyl, tetrahydrothiopyranyl,S-oxotetrahydrothiopyranyl, S-dioxotetrahydrothiopyranyl, morpholinyl,thiomorpholinyl, S-oxothiomorpholinyl, S-dioxothiomorpholinyl, thiazinyland the like. Examples for heterocyclic ring also comprising 1 or 2carbonyl groups as ring members comprise pyrrolidin-2-onyl,pyrrolidin-2,5-dionyl, imidazolidin-2-onyl, oxazolidin-2-onyl,thiazolidin-2-onyl and the like.

The term “ammonium” per se refers to the cation NH₄ ⁺. The expression“ammonium cations of primary, secondary or tertiary amines”, as usedsimilarly in the expression “primary, secondary, tertiary amines, andammonium salts thereof” refers to protonated primary, secondary ortertiary amines. The protonation of such ammonium cations is dependenton the pH and the positive charge varies accordingly. The term“quaternary ammonium (cat)ion(s)” refers to permanently positivelycharged cations containing a nitrogen atom with four organic bindingpartners, e.g. alkyl groups. Accordingly, the term “quaternary ammoniumsalt(s)” refers to a salt containing a quaternary ammonium cation.Examples of quaternary ammonium ions are tetramethylammonium,tetraethylammonium, tetraethanolammonium, cholin,2-hydroxyethyltrimethyl ammonium, and trishydroxyethylmethyl ammonium.

The liquid herbicidal composition contains a compound of formula (I)

[R-(A)_(x)-OSO₃ ⁻]-M⁺  (I);

whereinR is C₁₀-C₁₆-alkyl, C₁₀-C₁₆-alkenyl, or C₁₀-C₁₆-alkynyl;each A is independently a group

wherein

-   -   R^(A), R^(B), R^(C), and R^(D) are independently H, CH₃, or        CH₂CH₃ with the proviso that the sum of C-atoms of R^(A), R^(B),        R^(C), and R^(D) is up to 2;    -   M⁺ is a monovalent cation; and    -   the index x is a number from 1 to 10.

Compounds of formula (I) can be prepared by standard methods of organicchemistry. The anionic moiety (I-a)

R-(A)_(x)-OSO₃ ⁻  (I-a)

is commercially available in the form of sodium or potassium salts, e.g.under the tradename Genapol LRO from Clariant, and can be prepared asdescribed in U.S. Ser. No. 10/091,994B2, columns 1-2, which isincorporated herein by reference. Compounds of formula (I) are ioniccompounds that comprise the anionic moiety (I-a) and the monovalentcation M⁺, which is positively and singly charged.

The compounds of formula (I) may contain an ammonium cation M⁺ of aprimary, secondary, or tertiary amine, i.e. a protonated primary,secondary or tertiary amine, or a quaternary ammonium cation. Suchcompounds are available from the commercially available sodium orpotassium salts by ion exchange chromatography or other methods suitablefor ion exchange. Alternatively, compounds of formula (I), wherein M⁺ isNH₄ ⁺ or an ammonium cation of a primary, secondary, or tertiary amine,are available by reaction of compounds of formula (I) with SO₃ or CISO₃Hand subsequent addition of the respective amine base or ammonia M asdepicted in Scheme 1

wherein all variables have a meaning as defined for formula (I).Reactions of this type are typically carried out at temperatures of 50to 100° C. under addition of an excess of SO₃ or CISO₃H compared to theamount of compound of formula (I). Compounds of formula (I) arecommercially available under various tradenames, e.g. the Lutensol TOseries from BASF, and may be produced from the respective alcohols R—OHby alkoxylation with ethylene oxide, propylene oxide, or butylene oxideas described in U.S. Ser. No. 10/091,994B2. Amine bases M are equallycommercially available and form the respective ammonium cations M⁺ ofprimary, secondary, or tertiary amines in compounds of formula (I).

The monovalent cation M⁺ is thus typically selected from

α) alkali metal cations, e.g. Li⁺, Na⁺, and K⁺;β) NH₄ ⁺;γ) ammonium cations of a primary, secondary, and tertiary amines; andδ) quaternary ammonium cations.

In one embodiment, the monovalent cation M⁺ is an alkali metal cation orNH₄ ⁺. In another embodiment, the monovalent cation M⁺ is an alkalimetal cation, preferably Na⁺ or K⁺, more preferably Na⁺.

If the amine component contains an ammonium salt or a quaternaryammonium salt, the monovalent cation M⁺ is typically different from theammonium cation or quaternary ammonium cation in said ammonium salt orquaternary ammonium salt. Accordingly, M⁺ is typically different fromthe protonated amine component if the amine component is a primary,secondary or tertiary amine.

The variables of formula (I) have the following preferred meanings andembodiments. Combinations of such preferred meanings and embodiments ofall levels of preference are within the scope of the invention.

R is a C₁₀-C₁₆-alkyl, C₁₀-C₁₆-alkenyl, or C₁₀-C₁₆-alkenyl. Typically, Ris a C₁₀-C₁₆-alkyl, preferably C₁₀-C₁₄-alkyl, more preferablyC₁₁-C₁₃-alkyl, and in particular C₁₂-alkyl, such as linear C₁₂-alkyl. Inanother embodiment, R is C₁₀-C₁₆-alkenyl, preferably C₁₀-C₁₄-alkenyl,more preferably C₁₁-C₁₃-alkenyl, and in particular C₁₂-alkenyl. Inanother embodiment, R is C₁₀-C₁₆-alkynyl, preferably C₁₀-C₁₄-alkynyl,more preferably C₁₁-C₁₃-alkynyl, and in particular C₁₂-alkynyl.

Each A is independently a group

whereinR^(A), R^(B), R^(C), and R^(D) are independently H, CH₃, or CH₂CH₃ withthe proviso that the sum of C-atoms of R^(A), R^(B), R^(C), and R^(D) isup to 2.

Typically, the sum of C-atoms of R^(A), R^(B), R^(C), and R^(D) is upto 1. Preferably, R^(A), R^(B), R^(C) and R^(D) are H. Typically, eachgroup A is the same, preferably wherein R^(A), R^(B), R^(C) and R^(D)are H.

In one embodiment, a mixture of different groups A is present, such as amixture of groups A, wherein all substituents R^(A), R^(B), R^(C) andR^(D) are H, with groups A, wherein one substituent R^(A), R^(B), R^(C)or R^(D) is CH₃.

In another embodiment, a mixture of different groups A is present, suchas a mixture of groups A, wherein all substituents R^(A), R^(B), R^(C)and R^(D) are H, with groups A, wherein one substituent R^(A)R^(B),R^(C) or R^(D) is CH₂CH₃.

In case a mixture of different groups A is present, the molar ratio ofgroups A, wherein all substituents R^(A), R^(B), R^(C) and R^(D) are H,is typically at least 10 mol %, preferably at least 25 mol %, morepreferably at least 50 mol %, and in particular at least 80 mol %.

The index x is from 1 to 10. The index x represents a molar mean of allmolecules of compounds of formula (I) in a given ensemble and is anynumber from 1 to 10, including real numbers between 1 and 10. Theskilled person is aware that the common synthesis of compounds offormula (I) includes an alkoxylation step of alcohol R—OH, as outlinedabove, which alkoxylation step results in a statistical distribution ofspecies R-(A)_(x)-OH, and in turn results in a statistical distributionof compounds of formula (I) regarding the index x.

Typically, the index x is up to 8, preferably up to 6, more preferablyup to 4, most preferably up to 3. The index x may be at least 1.5,preferably at least 2. The index x is typically from 1 to 5, preferablyfrom 1 to 4, more preferably from 1 to 3, most preferably from 1.5 to 3,and in particular from 1.5 to 2.5.

In one embodiment, the substituents of formula (I) have the followingmeaning: R is C₁₀-C₁₄-alkyl;

each A is independently a group

wherein

-   R^(A), R^(B), R^(C), and R^(D) are independently H, CH₃, or CH₂CH₃    with the proviso that the sum of C-atoms of R^(A), R^(B), R^(C), and    R^(D) is up to 2;-   M⁺ is a monovalent cation; and-   the index x is a number from 1 to 5.

In another embodiment, the substituents of formula (I) have thefollowing meaning: R is C₁₀-C₁₄-alkyl;

each A is independently a group

whereinR^(A), R^(B), R¹, and R^(D) are H;M⁺ is a monovalent cation; andthe index x is a number from 1 to 5.

In another embodiment, the substituents of formula (I) have thefollowing meaning: R is C₁₀-C₁₄-alkyl;

each A is independently a group

whereinR^(A), R^(B), R^(C), and R^(D) are H;M⁺ is a monovalent cation; andthe index x is a number from 1 to 5.

In another embodiment, the substituents of formula (I) have thefollowing meaning: R is C₁₀-C₁₄-alkyl;

each A is independently a group

whereinR^(A), R^(B), R^(C), and R^(D) are H;M⁺ is a monovalent cation; andthe index x is a number from 1 to 5.

In another embodiment, the substituents of formula (I) have thefollowing meaning: R is C₁₂-alkyl, preferably linear C₁₂-alkyl;

each A is independently a group

whereinR^(A), R^(B), R^(C), and R^(D) are H:M⁺ is a monovalent cation; andthe index x is a number from 1 to 3.

In another embodiment, the substituents of formula (I) have thefollowing meaning: R is C₁₂-alkyl, preferably linear C₁₂-alkyl;

each A is independently a group

whereinR^(A), R^(B), R^(C), and R^(D) are H;the index x is a number from 1 to 3; andM⁺ is a monovalent cation selected from Na⁺, and K⁺.

In another embodiment, the substituents of formula (I) have thefollowing meaning: R is C₁₂-alkyl, preferably linear C₁₂-alkyl;

each A is independently a group

whereinR^(A), R^(B), R^(C), and R^(D) are H;the index x is a number from 1 to 3; andM⁺ is Na⁺.

The herbicidal composition may comprise the compound of formula (I) in aconcentration of at least 1 wt %, preferably at least 5 wt % morepreferably at least 10 wt %, most preferably at least 15 wt %, inparticular at least 20 wt %, and especially at least 30 wt %, such as atleast 40 wt % based on the total weight of the herbicidal composition.The herbicidal composition may comprise the compound of formula (I) in aconcentration of up to 90 wt %, preferably up to 70 wt %, morepreferably up to 50 wt % based on the total weight of the herbicidalcomposition. The herbicidal composition may comprise the compound offormula (I) in a concentration of from 5 to 70 wt %, preferably 5 to 60wt %, more preferably 10 to 50 wt %, most preferably 15 to 40 wt % basedon the total weight of the herbicidal composition. In one embodiment,the agrochemical composition comprises the compound of formula (I) in aconcentration of more than 25 wt %, preferably at least 26 wt %, morepreferably at least 27 wt %, especially at least 28 wt %, such as atleast 29 wt %.

The composition also contains an amine component selected from primary,secondary, tertiary amines, and ammonium salts thereof, and quaternaryammonium salts, wherein the molecular weight of the primary, secondaryor tertiary amines, of the ammonium cation in the ammonium salts, or ofthe quaternary ammonium cation in the quaternary ammonium salts is from32 to 200 g/mol. Such amine components are commercially available. Theamine component is commercially available or obtainable by standardmethods of organic chemistry.

In one embodiment, the amine component comprises a primary, secondary,tertiary amine or an ammonium salt thereof (i.e. the salt of aprotonated primary, secondary or tertiary amine). In another embodiment,the amine component is a quaternary ammonium salt. Typically, the aminecomponent contains only one nitrogen atom per molecule.

The molecular weight of the primary, secondary or tertiary amine, of theammonium cation in the ammonium salt or the quaternary ammonium cationin the quaternary ammonium salt, is from 32 to 200 g/mol. In oneembodiment, the molecular weight of the primary, secondary or tertiaryamine, of the ammonium cation in the ammonium salt or the quaternaryammonium cation in the quaternary ammonium salt, is from is at least 35g/mol. In another embodiment, the molecular weight of the primary,secondary or tertiary amine, of the ammonium cation in the ammonium saltor the quaternary ammonium cation in the quaternary ammonium salt, is atleast 40 g/mol. In another embodiment, the molecular weight of theprimary, secondary or tertiary amine, of the ammonium cation in theammonium salt or the quaternary ammonium cation in the quaternaryammonium salt, is at least 45 g/mol. In another embodiment, themolecular weight of the primary, secondary or tertiary amine, of theammonium cation in the ammonium salt or the quaternary ammonium cationin the quaternary ammonium salt, is at least 50 g/mol. In anotherembodiment, the molecular weight of the primary, secondary or tertiaryamine, of the ammonium cation in the ammonium salt or the quaternaryammonium cation in the quaternary ammonium salt is at least 55 g/mol. Inanother embodiment, the molecular weight of the primary, secondary ortertiary amine, of the ammonium cation in the ammonium salt or thequaternary ammonium cation in the quaternary ammonium salt, is at least60 g/mol. In another embodiment, the molecular weight of the primary,secondary or tertiary amine, of the ammonium cation in the ammonium saltor the quaternary ammonium cation in the quaternary ammonium salt in theammonium salt, is at least 61 g/mol. In one embodiment, the molecularweight of the primary, secondary or tertiary amine, of the ammoniumcation in the ammonium salt or the quaternary ammonium cation in thequaternary ammonium salt, is up to 195 g/mol. In another embodiment, themolecular weight of the primary, secondary or tertiary amine, of theammonium cation in the ammonium salt or the quaternary ammonium cationin the quaternary ammonium salt, is up to 190 g/mol g/mol. In anotherembodiment, the molecular weight of the primary, secondary or tertiaryamine, of the ammonium cation in the ammonium salt or the quaternaryammonium cation in the quaternary ammonium salt, is up to 185 g/mol. Inanother embodiment, the molecular weight of the primary, secondary ortertiary amine, of the ammonium cation in the ammonium salt or thequaternary ammonium cation in the quaternary ammonium salt, is up to 180g/mol. In another embodiment, the molecular weight of the primary,secondary or tertiary amine, of the ammonium cation in the ammonium saltor the quaternary ammonium cation in the quaternary ammonium salt, is upto 175 g/mol. In another embodiment, the molecular weight of theprimary, secondary or tertiary amine, of the ammonium cation in theammonium salt or the quaternary ammonium cation in the quaternaryammonium salt, is up to 170 g/mol. In another embodiment, the molecularweight of the primary, secondary or tertiary amine, of the ammoniumcation in the ammonium salt or the quaternary ammonium cation in thequaternary ammonium salt, is up to 160 g/mol. In another embodiment, themolecular weight of the primary, secondary or tertiary amine, of theammonium cation in the ammonium salt or the quaternary ammonium cationin the quaternary ammonium salt, is up to 150 g/mol. In anotherembodiment, the molecular weight of the primary, secondary or tertiaryamine, of the ammonium cation in the ammonium salt or the quaternaryammonium cation in the quaternary ammonium salt, is up to 140 g/mol. Inanother embodiment, the molecular weight of the primary, secondary ortertiary amine, of the ammonium cation in the ammonium salt or thequaternary ammonium cation in the quaternary ammonium salt, is up to 130g/mol. In another embodiment, the molecular weight of the primary,secondary or tertiary amine, of the ammonium cation in the ammonium saltor the quaternary ammonium cation in the quaternary ammonium salt, is upto 120 g/mol. In another embodiment, the molecular weight of theprimary, secondary or tertiary amine, of the ammonium cation in theammonium salt or the quaternary ammonium cation in the quaternaryammonium salt is up to 110 g/mol. In another embodiment, the molecularweight of the primary, secondary or tertiary amine, of the ammoniumcation in the ammonium salt or the quaternary ammonium cation in thequaternary ammonium salt is up to 105 g/mol. In one embodiment, themolecular weight of the primary, secondary or tertiary amine, of theammonium cation in the ammonium salt or the quaternary ammonium cationin the quaternary ammonium salt is from 35 g/mol to 150 g/mol. Inanother embodiment, the molecular weight of the primary, secondary ortertiary amine, of the ammonium cation in the ammonium salt or thequaternary ammonium cation in the quaternary ammonium salt is from 40g/mol to 140 g/mol. In another embodiment, the molecular weight of theprimary, secondary or tertiary amine, of the ammonium cation in theammonium salt or the quaternary ammonium cation in the quaternaryammonium salt is from 55 g/mol to 180 g/mol. In another embodiment, themolecular weight of the primary, secondary or tertiary amine, of theammonium cation in the ammonium salt or the quaternary ammonium cationin the quaternary ammonium salt is from 50 g/mol to 120 g/mol. In oneembodiment, the molecular weight of the primary, secondary or tertiaryamine, of the ammonium cation in the ammonium salt or the quaternaryammonium cation in the quaternary ammonium salt is from 55 g/mol to 110g/mol. In one embodiment, the molecular weight of the primary, secondaryor tertiary amine, of the ammonium cation in the ammonium salt or thequaternary ammonium cation in the quaternary ammonium salt is from 60g/mol to 110 g/mol.

The primary, secondary or tertiary amine N and the protonated ammoniumform N⁺ form a conjugated acid/base pair and are in equilibrium inaqueous conditions as displayed in Scheme 1

N+H₂O

N+H₃O⁺  Scheme 1:

The invention thus also pertains to a situation wherein the amine ispresent both in its protonated state N⁺ and in its non-protonated stateN.

The molar ratio of protonated amine N⁺ to non-protonated amine N istypically at least 1:1, preferably at least 3:1, more preferably atleast 5:1 most preferably at least 10:1. The molar ratio of protonatedamine N⁺ to non-protonated amine N is typically up to 50:1, preferablyup to 20:1, more preferably up to 15:1 most preferably up to 8:1.

The ratio is dependent of the pH of the liquid herbicidal composition.The pH is typically from 5 to 12, preferably from 6 to 10, morepreferably from 6.5 to 9. The pH may be adjusted by the addition of anacid, such as HCl, H₂SO₄, H₂SO₃, or methylsulfonic acid. By addition ofan acid, the amine N is protonated and present in the form of itsammonium salt, such as the chloride salt, the sulfate salt, thesulfonate salt, or the methyl sulfonate salt. Thus, the ammonium salt ofthe primary, secondary or tertiary amine is formed in situ by reactionof the acid with the amine N. Alternatively, the respective ammoniumsalt of the primary, secondary or tertiary amine may be added to thecomposition.

Since compounds of formula (I) are ionic compounds, and since the aminecomponent may contain, or form an ammonium salt, or contain a quaternaryammonium salt, the compounds of formula (I) and the amine component mayexchange their respective counterions in solution as displayed in Scheme2

[R-(A)_(x)-OSO₃ ⁻ ]-M⁺(I)+[B⁻]-[Q⁺]

[R-(A)_(x)-OSO₃ ⁻ ]-Q⁺(I-b)+[B⁻][M⁺]  Scheme 2:

wherein B⁻ is a monovalent anion, such as Cl⁻, SO₄ ⁻, SO₃ ⁻, or CH₃SO₃⁻, wherein Q⁺ is an ammonium cation of the primary, secondary, ortertiary amine, or a quaternary ammonium cation of the quaternaryammonium salt, and wherein all other variables have a meaning as definedfor formula (I). Ion exchange reactions of this type usually occur inliquid compositions and reach an equilibrium in which both the reactionyielding compounds of formula (I-b) and the backward reaction tocompounds of formula (I) are in equilibrium. Thus, the invention alsopertains to a situation in which the herbicidal composition containscompounds of formula (I) and compounds of formula (I-b) in any givenratio. For example, the molar ratio of compounds of formula (I) tocompounds of formula (I-b) may be from 100:1 to 1:100, preferably from10:1 to 1:10.

Accordingly, the herbicidal composition may contain a mixture ofcations, including monovalent cations M⁺ and the cations of the ammoniumsalt(s) of primary, secondary, and tertiary amine(s) and of thequaternary ammonium salts Q⁺. The invention thus also pertains to asituation in which the molar ratio of the monovalent cations M⁺ comparedto the cations Q⁺ as defined above is at least 1:100, preferably atleast 1:10, more preferably at least 1:1, most preferably at least 2:1,and in particular at least 10:1, such as at least 50:1. The molar ratioof cations M⁺ to cations Q⁺ may be from 100:1 to 1:100, preferably from20:1 to 1:20.

The invention also pertains to a situation in which the molarconcentration of the monovalent cations M⁺ compared to the total amountof the moiety (I-a) in the composition, either in the form of compoundof formula (I), as compound of formula (I-b) or as a different salt, isless than 100 mol-%. The molar concentration of the monovalent cation M⁺compared to the total amount of the moiety (I-a) is typically at least10 mol %, preferably at least 20 mol-%, more preferably at least 30mol-%, most preferably at least 50 mol-%, and in particular at least 80mol-%, such as at least 90 mol-%. Preferably the molar concentration ofthe monovalent cations M⁺ compared to the total amount of the moiety(I-a) is at least 99 mol-%, in particular 100 mol-%.

Preferable, the amine component the amine component contains a salt ofthe cation of formula (II) or a primary, secondary, or tertiary ammineof formula (III)

wherein

-   R¹, R², R⁴, R⁵, R⁶, and R⁷ are independently H, or C₁-C₁₀-alkyl,    which is unsubstituted or substituted with OH, C₁-C₁₀-alkoxy, or    hydroxy-C₁-C₁₀-alkoxy; or    -   two of the substituents R¹, R², R³, and R⁴, or of the        substituents R⁵, R⁶, and R⁷ form, together with the N-atom to        which they are bound, a 5-, or 6-membered, saturated, partially-        or fully unsaturated heterocycle containing additionally none,        one or two atoms O, or S, and wherein said S-atom(s) are        independently oxidized or non-oxidized,    -   with the proviso that at least one substituent R¹, R², R³, or R⁴        is not H; and    -   with the proviso that at least one substituent R⁵, R⁶, or R⁷ is        not H.

The sum of substituents R¹, R², R³, and R⁴ typically contain up to 18carbon atoms (“C-atoms”), preferably up to 16 C-atoms, more preferablyup to 14 C-atoms, most preferably up to 12 C-atoms, utmost preferably upto 10 C-Atom, in particular up to 8 C-atoms, such as up to 6 C-atoms.

In one embodiment, the sum of substituents R¹, R², R³ and R⁴ contain upto 9 C-atoms. In another embodiment, the sum of substituents R¹, R², R³and R⁴ contain up to 7 C-atoms. In another embodiment, the sum ofsubstituents R¹, R², R³ and R⁴ contain up to 5 C-atoms. In anotherembodiment, the sum of substituents R¹, R², R³ and R⁴ contain up to 4C-atoms. In another embodiment, the sum of substituents R¹, R² and R³contain up to 3 C-atoms.

The sum of substituents R¹, R² and R³ contain at least one C-atom,preferably at least 2 C-atoms, more preferably at least 3 C-atoms.

In one embodiment, the sum of substituents R¹, R², R³ and R⁴ containfrom 1 to 15 C-atoms. In another embodiment, the sum of substituents R¹,R², R³ and R⁴ contain from 1 to 12 C-atoms. In another embodiment, thesum of substituents R¹, R², R³ and R⁴ contain from 1 to 10 C-atoms. Inanother embodiment, the substituents R¹, R², R³, and R⁴ contain from 2to 12 C-atoms. In another embodiment, the sum of substituents R¹, R², R³and R⁴ contain from 2 to 10 C-atoms. In another embodiment, the sum ofsubstituents R¹, R², R³ and R⁴ contain from 1 to 6 C-atoms. In anotherembodiment, the substituents R¹, R², R³ and R⁴ contain from 1 to 4C-atoms. In another embodiment, the substituents R¹, R², R³ and R⁴contain from 1 to 3 C-atoms.

The sum of substituents R⁵, R⁶, and R⁷ typically contain up to 18 carbonatoms (“C-atoms”), preferably up to 16 C-atoms, more preferably up to 14C-atoms, most preferably up to 12 C-atoms, utmost preferably up to 10C-Atom, in particular up to 8 C-atoms, such as up to 6 C-atoms.

In one embodiment, the sum of substituents R⁵, R⁶, and R⁷ contain up to9 C-atoms. In another embodiment, the sum of substituents R⁵, R⁶, and R⁷contain up to 7 C-atoms. In another embodiment, the sum of substituentsR⁵, R⁶, and R⁷ contain up to 5 C-atoms. In another embodiment, the sumof substituents R⁵, R⁶, and R⁷ contain up to 4 C-atoms. In anotherembodiment, the sum of substituents R⁵, R⁶ and R⁷ contain up to 3C-atoms.

The sum of substituents R⁵, R⁶ and R⁷ contain at least one C-atom,preferably at least 2 C-atoms, more preferably at least 3 C-atoms.

In one embodiment, the sum of substituents R⁵, R⁶, and R⁷ contain from 1to 15 C-atoms. In another embodiment, the sum of substituents R⁵, R⁶,and R⁷ contain from 1 to 12 C-atoms. In another embodiment, the sum ofsubstituents R⁵, R⁶, and R⁷ contain from 1 to 10 C-atoms. In anotherembodiment, the substituents R⁵, R⁶, and R⁷ contain from 2 to 12C-atoms. In another embodiment, the sum of substituents R⁵, R⁶, and R⁷contain from 2 to 10 C-atoms. In another embodiment, the sum ofsubstituents R⁵, R⁶, and R⁷ contain from 1 to 6 C-atoms. In anotherembodiment, the substituents R⁵, R⁶, and R⁷ contain from 1 to 4 C-atoms.In another embodiment, the substituents R⁵, R⁶, and R⁷ contain from 1 to3 C-atoms.

In one embodiment R¹, R², R⁴, R⁵, R⁶, and R⁷ are independently H, orC₁-C₁₀-alkyl, which is unsubstituted or substituted with OH,C₁-C₁₀-alkoxy, or hydroxy-C₁-C₁₀-alkoxy, wherein at least onesubstituent R¹, R², R³, or R⁴ is not H, and wherein at least onesubstituent R⁵, R⁶, or R⁷ is not H.

In another embodiment R¹, R², R⁴, R⁵, R⁶, and R⁷ are independently H, orC₁-C₃-alkyl, which is unsubstituted or substituted with OH,C₁-C₃-alkoxy, or hydroxy-C₁-C₃-alkoxy, wherein at least one substituentR¹, R², R³, or R⁴ is not H, and wherein at least one substituent R⁵, R⁶,or R⁷ is not H.

In another embodiment R¹, R², R⁴, R⁵, R⁶, and R⁷ are independently H, orC₁-C₇-alkyl, which is unsubstituted or substituted with OH,C₁-C₄-alkoxy, or hydroxy-C₁-C₄-alkoxy, wherein at least one substituentR¹, R², R³, or R⁴ is not H, and wherein at least one substituent R⁵, R⁶,or R⁷ is not H.

In another embodiment R¹, R², R⁴, R⁵, R⁶, and R⁷ are independently H, orC₁-C₃-alkyl, which is unsubstituted or substituted with OH,C₁-C₃-alkoxy, or hydroxy-C₁-C₃-alkoxy, wherein at least one substituentR¹, R², R³, or R⁴ is not H, and wherein at least one substituent R⁵, R⁶,or R⁷ is not H.

In another embodiment R¹, R², R⁴, R⁵, R⁶, and R⁷ are independently H, orC₁-C₂-alkyl, which is unsubstituted or substituted with OH,C₁-C₂-alkoxy, or hydroxy-C₁-C₂-alkoxy, wherein at least one substituentR¹, R², R³, or R⁴ is not H, and wherein at least one substituent R⁵, R⁶,or R⁷ is not H.

In another embodiment, two of the substituents R¹, R², R³ and R⁴, or ofthe substituents R⁵, R⁶, and R⁷ form, together with the N-atom to whichthey are bound, a 5-, or 6-membered, saturated, partially- or fullyunsaturated heterocycle containing additionally none, one or two atomsO, or S, and wherein said S-atom(s) are independently oxidized ornon-oxidized, and the remaining substituents are either H, orC₁-C₁₀-alkyl, which is unsubstituted or substituted with OH,C₁-C₁₀-alkoxy, or hydroxy-C₁-C₁₀-alkoxy.

In another embodiment, two of the substituents R¹, R², R³ and R⁴, or ofthe substituents R⁵, R⁶, and R⁷ form, together with the N-atom to whichthey are bound, a 5-, or 6-membered, saturated, partially- or fullyunsaturated heterocycle containing additionally none, one or two atomsO, or S, and wherein said S-atom(s) are independently oxidized ornon-oxidized, and the remaining substituents are either H, orC₁-C₄-alkyl, which is unsubstituted or substituted with OH,C₁-C₄-alkoxy, or hydroxy-C₁-C₄-alkoxy.

In another embodiment, two of the substituents R¹, R², R³ and R⁴, or ofthe substituents R⁵, R⁶, and R⁷ form, together with the N-atom to whichthey are bound, a 5-, or 6-membered, saturated, partially- or fullyunsaturated heterocycle containing additionally none, one or two atomsO, or S, and wherein said S-atom(s) are independently oxidized ornon-oxidized, and the remaining substituents are either H, orC₁-C₃-alkyl, which is unsubstituted or substituted with OH,C₁-C₃-alkoxy, or hydroxy-C₁-C₃-alkoxy.

In another embodiment, two of the substituents R¹, R², R³ and R⁴, or ofthe substituents R⁵, R⁶, and R⁷ form, together with the N-atom to whichthey are bound, a 5-, or 6-membered, saturated, partially- or fullyunsaturated heterocycle containing additionally none, one or two atomsO, or S, and wherein said S-atom(s) are independently oxidized ornon-oxidized, and the remaining substituents are either H, orC₁-C₂-alkyl, which is unsubstituted or substituted with OH,C₁-C₂-alkoxy, or hydroxy-C₁-C₂-alkoxy.

The amine component is typically an amine selected from ethanolamine(also called monoethanolamine, CAS number 141-43-5), diethanolamine,diglycolamine, 1-aminopropan-2-ol, 2-dimethylaminoethanol,2-(butylamino)ethanol, 2-diethylaminoethanol,2-(tert-butylamino)-ethanol, N-(tert-butyl)diethanolamine,triethanolamine, 2-ethylaminoethanol, 2-aminoheptane, triisopropylamine,N-(2-hydroxyethyl)morpholin, N-methylmorpholine, N-butyldiethanolamin,2-(dibutylamino)ethanol, or an ammonium salt thereof, i.e. the salt of aprotonated amine selected from those above. In another embodiment, theamine component is a salt of a quaternary ammonium cation selected from2-hydroxyethyltrimethyl ammonium, trishydroxyethylmethyl ammonium.

Salts of quaternary ammonium cations may contain any suitable mono, ordivalent anion, preferably monovalent anion. Examples of anions arenitrate, sulfate, chloride, bromide, iodide, carbonate, bicarbonate,acetate, formate, phosphate and phosphonate. In one embodiment, thequaternary ammonium cation contains chloride as anion.

In one embodiment, the amine component is ethanolamine or an ammoniumsalt thereof. In another embodiment, the amine component isdiethanolamine or an ammonium salt thereof. In another embodiment, theamine component is diglycolamine or an ammonium salt thereof. In anotherembodiment, the amine component is 1-aminopropan-2-ol or an ammoniumsalt thereof. In another embodiment, the amine component is2-dimethylaminoethanol or an ammonium salt thereof. In anotherembodiment, the amine component is 2-(butylamino)ethanol or an ammoniumsalt thereof. In another embodiment, the amine component is protonated2-diethylaminoethanol or an ammonium salt thereof. In anotherembodiment, the amine component is 2-(tert-butylamino)ethanol or anammonium salt thereof. In another embodiment, the amine component isN-(tert-butyl)diethanolamine or an ammonium salt thereof. In anotherembodiment, the amine component is triethanolamine or an ammonium saltthereof. In another embodiment, the amine component is2-ethylaminoethanol or an ammonium salt thereof. In another embodiment,the amine component is 2-aminoheptan or an ammonium salt thereof. Inanother embodiment, the amine component is triisopropylamine or anammonium salt thereof.

In another embodiment, the amine component isN-(2-hydroxyethyl)morpholin or an ammonium salt thereof, In anotherembodiment, the amine component is N-methylmorpholine or an ammoniumsalt thereof. In another embodiment, the amine component is protonatedN-butyl-diethanolamine or an ammonium salt thereof. In anotherembodiment, the amine component is 2-(dibutylamino)ethanol or anammonium salt thereof. In another embodiment, the amine component is asalt of 2-hydroxyethyltrimethyl ammonium. In another embodiment, theamine component is a salt of trishydroxyethylmethyl ammonium.

In another embodiment, the amine component is selected fromethanolamine, diethanolamine, diglycolamine, 1-aminopropan-2-ol,2-dimethylaminoethanol, or an ammonium salt thereof, or a salt oftrishydroxyethylmethyl ammonium. In another embodiment, the aminecomponent is selected from ethanolamine, diglycolamine, triethanolamine,and ammonium salts thereof, and a salt of 2-hydroxyethyltrimethylammonium.

The herbicidal composition may comprise the amine component in aconcentration of at least 1 wt %, preferably at least 5 wt % morepreferably at least 10 wt %, most preferably at least 15 wt %, inparticular at least 20 wt %, and especially at least 30 wt %, such as atleast 40 wt % based on the total weight of the herbicidal composition.The herbicidal composition may comprise the amine component in aconcentration of up to 90 wt %, preferably up to 70 wt %, morepreferably up to 50 wt % based on the total weight of the herbicidalcomposition. The herbicidal composition may comprise the amine componentin a concentration of from 5 to 70 wt %, preferably 5 to 50 wt %, morepreferably 10 to 50 wt %, most preferably 15 to 40 wt % based on thetotal weight of the herbicidal composition.

The liquid herbicidal composition comprises glufosinate or a saltthereof. Glufosinate (CAS Reg. No. 51276-47-2), with IUPAC-Name(2RS)-2-amino-4-[hydroxy(methyl)phosphinoyl]butyric acid, or4-[hydroxy(methyl)phosphinoyl]-DL-homoalanine) orDL-4-[hydroxyl(methyl)-phosphinoyl]-DL-homoalaninate, is known, as wellas agronomically acceptable salts thereof, in particularglufosinate-ammonium (IUPAC-Name: ammonium(2RS)-2-amino-4-(methylphosphinato)butyric acid, CAS Reg. No.77182-82-2). U.S. Pat. No. 4,168,963 describes phosphorus-containingcompounds with herbicidal activity, of which, in particular,phosphinothricin (2-amino-4-[hydroxy(methyl)phosphinoyl]butanoic acid;common name: glufosinate) and its salts have acquired commercialimportance in the agrochemistry (agricultural chemistry) sector.

For example, glufosinate and its salts—such as glufosinate ammonium—andits herbicidal activity have been described e.g. by F. Schwerdtle et al.Z. Pflanzenkr. Pflanzenschutz, 1981, Sonderheft IX, pp. 431-440.

Glufosinate as racemate and its salts are commercially available underthe tradenames Basta™ and Liberty™.

Glufosinate is represented by the following structure (IV):

The compound of formula (IV) is a racemate.

Glufosinate is a racemate of two enantiomers, out of which only oneshows sufficient herbicidal activity (see e.g. U.S. Pat. No. 4,265,654and JP92448/83). Even though various methods to prepare L-glufosinate(and respective salts) are known, the mixtures known in the art do notpoint at the stereochemistry, meaning that the racemate is present (e.g.WO 2003024221, WO2011104213, WO 2016113334, WO 2009141367).

In one embodiment, the herbicidal composition comprises racemicglufosinate mixtures as described above, wherein the glufosinatecomprises about 50% by weight of the L-enantiomer and about 50% byweight of the D-enantiomer. In another embodiment, the herbicidalcomposition comprises glufosinate, wherein at least 70% by weight of theglufosinate is L-glufosinate or a salt thereof.

L-glufosinate, with IUPAC-Name(2S)-2-amino-4-[hydroxy(methyl)phosphinoyl]butyric acid (CAS Reg. No.35597-44-5) and also called glufosinate-P, can be obtained commerciallyor may be pre-pared for example as described in WO2006/104120, U.S. Pat.No. 5,530,142, EP0248357A2, EP0249188A2, EP0344683A2, EP0367145A2,EP0477902A2, EP0127429 and J. Chem. Soc. Perkin Trans. 1, 1992,1525-1529.

Preferably, the salts of glufosinate or (L)-glufosinate are the sodium,potassium or ammonium (NH₄ ⁺) salts of glufosinate or L-glufosinate, inparticular glufosinate-P-ammonium (IUPAC-Name: ammonium(2S)-2-amino-4-(methylphosphinato)butyric acid, CAS Reg. No.73777-50-1), glufosinate-P-sodium (IUPAC-Name: sodium(2S)-2-amino-4-(methylphosphinato)butyric acid; CAS Reg. No. 70033-13-5)and glufosinate-P-potassium (IUPAC-Name: potassium(2S)-2-amino-4-(methylphosphinato)butyric acid) for L-glufosinate.

Hence, mixtures according to the herbicidal composition may contain(L)-glufosinate-ammonium or (L)-glufosinate-sodium or(L)-glufosinate-potassium as (L)-glufosinate salts and (L)-glufosinateas free acid, preferably (L)-glufosinate. Especially preferred areherbicidal compositions, which contain (L)-glufosinate-ammonium, i.e.the ammonium (NH₄ ⁺) salt of glufosinate.

The term “glufosinate” as used in the present invention typicallycomprises, in one embodiment of the invention, about 50% by weight ofthe L-enantiomer and about 50% by weight of the D-enantiomer; and inanother embodiment of the invention, more than 70% by weight of theL-enantiomer; preferably more than 80% by weight of the L-enantiomer;more preferably more than 90% of the L-enantiomer, most preferably morethan 95% of the L-enantiomer and can be prepared as referred to above.

Preferably, the herbicidal composition comprises an agrochemicallyeffective amount of the glufosinate or salt thereof. The term “effectiveamount” denotes an amount of an agrochemically active ingredient orcomposition, which is sufficient to achieve a biological effect, such ascontrolling harmful fungi on cultivated plants or in the protection ofmaterials and which does not result in a substantial damage to thetreated plants. Such an amount can vary in a broad range and isdependent on various factors, such as the pest species to be controlled,the treated cultivated plant or material, the climatic conditions andthe specific agrochemical active ingredient used.

The herbicidal composition may comprise the glufosinate, or a saltthereof, in a concentration of at least 1 wt %, preferably at least 5 wt% more preferably at least 10 wt %, most preferably at least 15 wt %, inparticular at least 20 wt %, and especially at least 25 wt %, such as atleast 30 wt % based on the total weight of the herbicidal composition.The herbicidal composition may comprise the glufosinate, or a saltthereof, in a concentration of up to 90 wt %, preferably up to 70 wt %,more preferably up to 50 wt % based on the total weight of theherbicidal composition.

The herbicidal composition may comprise the glufosinate, or a saltthereof, in a concentration of from 5 to 70 wt %, preferably 5 to 50 wt%, more preferably 10 to 50 wt %, most preferably 15 to 40 wt % based onthe total weight of the herbicidal composition.

Accordingly, in one embodiment, the invention relates to a herbicidalcomposition comprising

a) L-glufosinate, or a salt thereof;b) an amine component selected from primary, secondary, tertiary amines,and ammonium salts thereof, and quaternary ammonium salts;wherein the molecular weight of the primary, secondary or tertiaryamines, of the ammonium cation in the ammonium salts, or the quaternaryammonium cation in the quaternary ammonium salts, is from 32 to 200g/mol;c) a compound of formula (I)

[R-(A)_(x)-OSO₃ ⁻]-M⁺  (I);

whereinR is C₁₀-C₁₆-alkyl, C₁₀-C₁₆-alkenyl, or C₁₀-C₁₆-alkynyl;each A is independently a group

wherein

-   -   R^(A), R^(B), R^(C), and R^(D) are independently H, CH₃, or        CH₂CH₃ with the proviso that the sum of C-atoms of R^(A), R^(B),        R^(C), and R^(D) is up to 2;    -   M⁺ is a monovalent cation; and    -   the index x is a number from 1 to 10.

In another embodiment, the invention relates to a herbicidal compositioncomprising

-   a) L-glufosinate or a salt thereof;-   b) an amine component selected from primary, secondary, tertiary    amines, and ammonium salts thereof, and quaternary ammonium salts;    -   wherein the molecular weight of the primary, secondary or        tertiary amines, of the ammonium cation in the ammonium salts,        or the quaternary ammonium cation in the quaternary ammonium        salts, is from 32 to 200 g/mol;-   c) a compound of formula (I), wherein    R is C₁₀-C₁₄-alkyl;    each A is independently a group

whereinR^(A), R^(B), R^(C), and R^(D) are H;M⁺ is monovalent cation; andthe index x is a number from 1 to 5.

In another embodiment, the invention relates to a herbicidal compositioncomprising

-   a) L-glufosinate or a salt thereof;-   b) an amine component selected from primary, secondary, tertiary    amines, and ammonium salts thereof, and quaternary ammonium salts;    -   wherein the molecular weight of the primary, secondary or        tertiary amines, of the ammonium cation in the ammonium salts,        or the quaternary ammonium cation in the quaternary ammonium        salts, is from 32 to 200 g/mol;-   c) a compound of formula (I), wherein    R is C₁₂-alkyl, preferably linear C₁₂-alkyl;    each A is independently a group

whereinR^(A), R^(B), R^(C), and R^(D) are H;M⁺ is monovalent cation; andthe index x is a number from 1 to 3.

In another embodiment, the invention relates to a herbicidal compositioncomprising

a) L-glufosinate or a salt thereof;b) an amine component selected from salts of the cation of formula (II)and from primary, secondary, and tertiary ammines of formula (III)

wherein

-   R¹, R², R⁴, R⁵, R⁶, and R⁷ are independently H, or C₁-C₁₀-alkyl,    which is unsubstituted or substituted with OH, C₁-C₁₀-alkoxy, or    hydroxy-C₁-C₁₀-alkoxy; or    -   two of the substituents R¹, R², R³, and R⁴, or of the        substituents R⁵, R⁶, and R⁷ form, together with the N-atom to        which they are bound, a 5-, or 6-membered, saturated, partially-        or fully unsaturated heterocycle containing additionally none,        one or two atoms O, or S, and wherein said S-atom(s) are        independently oxidized or non-oxidized,    -   with the proviso that at least one substituent R¹, R², R³, or R⁴        is not H; and    -   with the proviso that at least one substituent R⁵, R⁶, or R⁷ is        not H;        wherein the molecular weight of the primary, secondary or        tertiary amine, or of the ammonium cation in the ammonium salt,        is from 32 to 200 g/mol;        c) a compound of formula (I), wherein        R is C₁₂-alkyl;        each A is independently a group

whereinR^(A), R^(B), R^(C), and R^(D) are H;M⁺ is Na⁺; andthe index x is a number from 1 to 3.

In another embodiment, the invention relates to a herbicidal compositioncomprising

-   a) the ammonium salt of L-glufosinate;-   b) an amine component selected from ethanolamine, diethanolamine,    diglycolamine, 1-aminopropan-2-ol, 2-dimethylaminoethanol,    2-(butylamino)ethanol, 2-diethylaminoethanol,    2-(tert-butylamino)ethanol, N-(tert-butyl)diethanolamine,    triethanolamine, 2-ethylaminoethanol, 2-aminoheptane,    triisopropylamine, N-(2-hydroxyethyl)morpholin, N-methylmorpholine,    N-butyldiethanolamin, 2-(dibutylamino)ethanol, and ammonium salts    thereof;    -   and salts of a quaternary ammonium cation selected from        2-hydroxyethyltrimethyl ammonium, trishydroxyethylmethyl        ammonium;    -   and mixtures thereof.        wherein the molecular weight of the primary, secondary or        tertiary amine, of the ammonium cation in the ammonium salt, or        of the quaternary ammonium cation in the quaternary ammonium        salt is from 32 to 200 g/mol;-   c) a compound of formula (I), wherein    R is C₁₂-alkyl, preferably linear C₁₂-alkyl;    each A is independently a group

whereinR^(A), R^(B), R^(C), and R^(D) are H;M⁺ is Na⁺; andthe index x is a number from 1 to 3.

In another embodiment, the invention relates to a herbicidal compositioncomprising

-   a) the ammonium salt of L-glufosinate;-   b) an amine component selected from ethanolamine, diethanolamine,    diglycolamine, 1-aminopropan-2-ol, 2-dimethylaminoethanol,    2-(butylamino)ethanol, 2-diethylaminoethanol,    2-(tert-butylamino)ethanol, N-(tert-butyl)diethanolamine,    triethanolamine, 2-ethylaminoethanol, 2-aminoheptane,    triisopropylamine, N-(2-hydroxyethyl)morpholin, N-methylmorpholine,    N-butyldiethanolamin, 2-(dibutylamino)ethanol, and ammonium salts    thereof;    -   and salts of a quaternary ammonium cation selected from        2-hydroxyethyltrimethyl ammonium, trishydroxyethylmethyl        ammonium;    -   and mixtures thereof.        wherein the molecular weight of the primary, secondary or        tertiary amine, of the ammonium cation in the ammonium salt, or        of the quaternary ammonium cation in the quaternary ammonium        salt is from 32 to 200 g/mol;-   c) a compound of formula (I), wherein    R is C₁₂-alkyl, preferably linear C₁₂-alkyl;    each A is independently a group

whereinR^(A), R^(B), R^(C), and R^(D) are H;M⁺ is a monovalent cation; andthe index x is a number from 1 to 3.

The following clauses C1 to C15 relate to preferred embodiments andcombinations of embodiments

-   C1) A liquid herbicidal composition comprising    -   a) glufosinate, or a salt thereof;    -   b) an amine component selected from primary, secondary, tertiary        amines, and ammonium salts thereof, and quaternary ammonium        salts;    -   wherein the molecular weight of the primary, secondary or        tertiary amines, of the ammonium cation in the ammonium salts,        or of the quaternary ammonium cation in the quaternary ammonium        salts is from 32 to 200 g/mol;    -   c) a compound of formula (I)

[R-(A)_(x)-OSO₃ ⁻]-M⁺  (I);

-   -   wherein    -   R is C₁₀-C₁₆-alkyl, C₁₀-C₁₆-alkenyl, or C₁₀-C₁₆-alkynyl;    -   each A is independently a group

-   -   wherein        -   R^(A), R^(B), R^(C), and R^(D) are independently H, CH₃, or            CH₂CH₃ with the proviso that the sum of C-atoms of R^(A),            R^(B), R^(C), and R^(D) is up to 2;    -   M⁺ is a monovalent cation; and    -   the index x is a number from 1 to 10.

-   C2) The composition according to C1, wherein the index x is from 1    to 3.

-   C3) The composition according to any of C1 or C2, wherein R^(A),    R^(B), R^(C), and R^(D) are H.

-   C4) The composition according to any of C1 to C3, wherein the    molecular weight of the primary, secondary, tertiary amine, or the    ammonium cation of the ammonium salt thereof or of the quaternary    ammonium salt is from 55 to 180 g/mol.

-   C5) The composition according to any of C1 to C4, wherein the    primary, secondary, or tertiary amine, or the ammonium salt thereof,    or the quaternary ammonium salt, contains exactly one nitrogen atom    per molecule.

-   C6) The composition according to any of C1 to C5, wherein M⁺ is Na⁺.

-   C7) The composition according to any of C1 to C6, wherein the amine    component contains a salt of the cation of formula (II) or a    primary, secondary, or tertiary ammine of formula (III)

-   -   wherein    -   R¹, R², R³, R⁴, R⁵, R⁶, and R⁷ are independently H, or        C₁-C₁₀-alkyl, which is unsubstituted or substituted with OH,        C₁-C₁₀-alkoxy, or hydroxy-C₁-C₁₀-alkoxy; or    -   two of the substituents R¹, R², R³, and R⁴, or of the        substituents R⁵, R⁶, and R⁷ form, together with the N-atom to        which they are bound, a 5-, or 6-membered, saturated, partially-        or fully unsaturated heterocycle containing additionally none,        one or two atoms O, or S, and wherein said S-atom(s) are        independently oxidized or non-oxidized,    -   with the proviso that at least one substituent R¹, R², R³, or R⁴        is not H; and    -   with the proviso that at least one substituent R⁵, R⁶, or R⁷ is        not H.

-   C8) The composition of C7, wherein the sum of R¹, R², R³ and R⁴, or    the sum of R⁵, R⁶, and R⁷ comprises from 1 to 12 carbon atoms.

-   C9) The composition according to any of C1 to C8, wherein the amine    component is an amine selected from    -   ethanolamine, diethanolamine, diglycolamine, 1-aminopropan-2-ol,        2-dimethylaminoethanol, 2-(butylamino)ethanol,        2-diethylaminoethanol, 2-(tert-butylamino)-ethanol,        N-(tert-butyl)diethanolamine, triethanolamine,        2-ethylaminoethanol, 2-aminoheptane, triisopropylamine,        N-(2-hydroxyethyl)morpholin, N-methylmorpholine,        N-butyldiethanolamin, 2-(dibutylamino)ethanol, and ammonium        salts thereof;    -   or a salt of a quaternary ammonium cation selected from        2-hydroxyethyltrimethyl ammonium, trishydroxyethylmethyl        ammonium;    -   or a mixture thereof.

-   C10) The composition according to any of C1 to C9, wherein the amine    component is an amine selected from ethanolamine, diethanolamine,    diglycolamine, 1-aminopropan-2-ol, 2-dimethylaminoethanol, or an    ammonium salt thereof, or a salt of trishydroxyethylmethyl ammonium.

-   C11) The composition according to any of C1 to C10, wherein the pH    is from 6 to 10.

-   C12) The composition according to any of C1 to C11, wherein the    amine component is a chloride, sulfate, sulfonate, or    methylsulfonate salt of a primary, secondary, or tertiary ammonium    cation.

-   C13) The composition according to any of C1 to C12, wherein the    component a) is the ammonium salt of glufosinate.

-   C14) The composition according to any of C1 to C13, comprising    -   a) 5 to 50 wt % of glufosinate, (L)-glufosinate, or a salt        thereof;    -   b) 5 to 50 wt % of the amine component;    -   c) 5 to 60 wt % of the compound of formula (I).

-   C15) The composition according to any of C1 to C14 containing a    second agrochemical active ingredient selected from herbicides of    classes b1) to b15) and safeners C).

The molar ratio of the glufosinate to the amine component is typicallyfrom 100:1 to 1:100, preferably from 50:1 to 1:50, more preferably from10:1 to 1:10, most preferably from 5:1 to 1:5.

The molar ratio of the amine component to the compound of formula (I)may be from 100:1 to 1:100, preferably 50:1 to 1:50, more preferably 5:1to 1:20.

The herbicidal composition relates to any liquid customary types ofagrochemical compositions, e. g. solutions, emulsions, or suspensions.Typically, the amine component and the compound of formula (I) arepresent in dissolved form in the composition. In one embodiment, theglufosinate or salt thereof is present in dissolved form. In anotherembodiment, the glufosinate or salt thereof is present in particulateform as suspended solid particles, e.g. with a particles size (d50) offrom 0.1 to 15 μm.

Examples for composition types are solutions, suspensions (e.g. SC, OD,FS), emulsifiable concentrates (e.g. EC), and emulsions (e.g. EW, EO,ES, ME), and capsule formulations (e.g. CS, ZC). These and furthercompositions types are defined in the “Catalogue of pesticideformulation types and international coding system”, Technical MonographNo. 2, 6^(th) Ed. May 2008, CropLife International. The herbicidalcomposition is a liquid composition, i.e. it contains a liquidcontinuous phase. Typically, the herbicidal composition is an aqueousherbicidal composition or a herbicidal composition with a continuousoily phase containing a non-aqueous organic solvent. Preferredformulation types of the herbicidal composition are solutions,emulsifiable concentrates, and dispersions, more preferably aqueoussolutions. Typically, the components of the herbicidal composition, i.e.the glufosinate or a salt thereof, the amine component, and the compoundof formula (I) are present in dissolved state in the herbicidalcomposition. The agrochemical active ingredient is typically eitherpresent in dissolved or in suspended form in the herbicidal composition.If the herbicidal composition is an aqueous composition, theagrochemical active ingredient is typically dissolved. If the herbicidalcomposition is an oily composition, the agrochemical active ingredientis typically present in particulate form as suspended particles, inparticular in oil dispersions.

Accordingly, the herbicidal composition may comprise water. Typically,the herbicidal composition comprises water in a concentration of atleast 1 wt %, preferably at least 5 wt, more preferably at least 10 wt%, most preferably at least 20 wt %. The herbicidal composition maycomprise water in a concentration of up to 50 wt %, preferably up to 40wt %, more preferably up to 30 wt %, and in particular up to 25 wt %.The herbicidal composition typically comprises water in a concentrationof from 1 to 50 wt %, preferably from 5 to 30 wt %. If the concentrationof water in the herbicidal composition is at least 5 wt %, suchcompositions may be referred to as aqueous compositions.

The herbicidal composition may also comprise at least one organicsolvent. Typically, the herbicidal composition comprises the organicsolvent in a concentration of at least 1 wt %, preferably at least 5 wt,more preferably at least 15 wt %. The herbicidal composition maycomprise the organic solvent in a concentration of up to 60 wt %,preferably up to 50 wt %, more preferably up to 45 wt %, and inparticular up to 35 wt %. The herbicidal composition typically comprisesthe organic solvent in a concentration of from 5 to 50 wt %, preferablyfrom 10 to 40 wt %. If the concentration of water in the herbicidalcomposition is at least 20 wt %, such compositions may be referred to as“oily” compositions. Suitable organic solvents are defined herein below.Preferred are such organic solvents that have a water-solubility of atleast 1 wt % at 20° C., preferably at least 10 wt % at 20° C.

Suitable organic solvents are aliphatic hydrocarbons, preferably analiphatic C₅-C₁₆-hydrocarbon, more preferably a C₅-C₁₆-alkane, orC₅-C₁₆-cycloalkane, such as pentane, hexane, cyclohexane, or petrolether; aromatic hydrocarbons, preferably an aromaticC₆-C₁₀-hydrocarbons, such as benzene, toluene, o-, m-, and p-xylene;halogenated hydrocarbons, preferably halogenated aliphaticC₁-C₆-alkanes, or halogenated aromatic C₆-C₁₀-hydrocarbons, such asCH₂Cl₂, CHCl₃, CCl₄, CH₂ClCH₂Cl, CCl₃CH₃, CHCl₂CH₂Cl, CCl₂CCl₂, orchlorobenzene; ethers, preferably C₁-C₆-cycloalkyl ethers,C₁-C₆-alkyl-C₁-C₆-alkyl ethers and C₁-C₆-alkyl-C₆-C₁₀-aryl ethers, suchas CH₃CH₂OCH₂CH₃, (CH₃)₂CHOCH(CH₃)₂, CH₃OC(CH₃)₃ (MTBE), CH₃OCH₃ (DME),CH₃OCH₂CH₂OCH₃, dioxane, anisole, and tetrahydrofurane (THF); esters,preferably esters of aliphatic C₁-C₆-alcohols with aliphaticC₁-C₆-carboxylic acids, esters of aromatic C₆-C₁₀-alcohols with aromaticC₆-C₁₀-carboxylic acids, cyclic esters of ω-hydroxy-C₁-C₆-carboxylicacids, such as CH₃C(O)OCH₂CH₃, CH₃C(O)OCH₃, CH₃C(O)OCH₂CH₂CH₂CH₃,CH₃C(O)OCH(CH₃)CH₂CH₃, CH₃C(O)OC(CH₃), CH₃CH₂CH₂C(O)OCH₂CH₃,CH₃CH(OH)C(O)OCH₂CH₃, CH₃CH(OH)C(O)OCH₃, CH₃C(O)OCH₂CH(CH₃)₂,CH₃C(O)OCH(CH₃)₂, CH₃CH₂C(O)OCH₃, benzyl benzoate, and γ-butyrolactone;carbonates, such as ethylene carbonate, propylene carbonate,CH₃CH₂OC(O)OCH₂CH₃, and CH₃OC(O)OCH₃; nitriles, preferablyC₁-C₆-nitriles, such as CH₃CN, and CH₃CH₂CN; ketones, preferablyC₁-C₆-alkyl-C₁-C₆-alkyl ketones, such as CH₃C(O)CH₃, CH₃C(O)CH₂CH₃,CH₃CH₂C(O)CH₂CH₃, and CH₃C(O)C(CH₃)₃ (MTBK); alcohols, preferablyC₁-C₄-alcohols, such as CH₃OH, CH₃CH₂OH, CH₃CH₂CH₂OH, CH₃CH(OH)CH₃,CH₃(CH₂)₃OH, C(CH₃)₃OH, propylene glycol, dipropylene glycol, propyleneglycol monomethylether (1-methoxy-2-propanol); amides and ureaderivatives, preferably dimethyl formamide (DMF), N-methyl-2-pyrrolidone(NMP), dimethyl acetamide (DMA), 1,3-dimethyl-2-imidazolidinone (DMI),1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU),hexamethylphosphamide (HMPA); moreover dimethyl sulfoxide (DMSO), andsulfolane. Preferred solvents are propylene glycol, dipropylene glycoland propyleneglycol monomethyl ether, more preferred propylene glycoland dipropylene glycol.

The herbicidal compositions are prepared in a known manner, such asdescribed by Mollet and Grubemann, Formulation technology, Wiley VCH,Weinheim, 2001; or Knowles, New developments in crop protection productformulation, Agrow Reports DS243, T&F Informa, London, 2005. Theinvention also relates to a method of producing the herbicidalcomposition comprising the step of contacting the amine component withthe compound of formula (I) and glufosinate or a salt thereof in anygiven order. In one embodiment, the method of producing the herbicidalcomposition comprises the steps of a) contacting the amine componentwith the compound of formula (I); and b) contacting the glufosinate, ora salt thereof with the compound of formula (I), wherein steps a) and b)may be carried out in any given order. Typically, the method forproducing the herbicidal composition also includes a step of addingwater at either stage of the method.

The herbicidal composition typically comprises at least one auxiliary.Suitable auxiliaries are solvents, liquid carriers, solid carriers orfillers, surfactants, dispersants, emulsifiers, wetters, adjuvants,solubilizers, penetration enhancers, protective colloids, adhesionagents, thickeners, humectants, repellents, attractants, feedingstimulants, compatibilizers, bactericides, anti-freezing agents,anti-foaming agents, colorants, tackifiers and binders.

Suitable solvents and liquid carriers are water and organic solvents asdefined herein below. Suitable solid carriers or fillers are mineralearths, e.g. silicates, silica gels, talc, kaolins, limestone, lime,chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate,magnesium sulfate, magnesium oxide; polysaccharides, e.g. cellulose,starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammoniumnitrate, ureas; products of vegetable origin, e.g. cereal meal, treebark meal, wood meal, nutshell meal, and mixtures thereof.

Suitable surfactants are surface-active compounds, such as anionic,cationic, nonionic and amphoteric surfactants, block polymers,polyelectrolytes, and mixtures thereof. Such surfactants can be used asemulsifier, dispersant, solubilizer, wetter, penetration enhancer,protective colloid, or adjuvant. Examples of surfactants are listed inMcCutcheon's, Vol. 1: Emulsifiers & Detergents, McCutcheon'sDirectories, Glen Rock, USA, 2008 (International Ed. or North AmericanEd.).

Suitable anionic surfactants are alkali, alkaline earth or ammoniumsalts of sulfonates, sulfates, phosphates, carboxylates, and mixturesthereof. Examples of sulfonates are alkylarylsulfonates,diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates,sulfonates of fatty acids and oils, sulfonates of ethoxylatedalkylphenols, sulfonates of alkoxylated arylphenols, sulfonates ofcondensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes,sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates orsulfosuccinamates. Examples of sulfates are sulfates of fatty acids andoils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols,or of fatty acid esters. Examples of phosphates are phosphate esters.Examples of carboxylates are alkyl carboxylates, and carboxylatedalcohol or alkylphenol ethoxylates.

Suitable nonionic surfactants are alkoxylates, N-substituted fatty acidamides, amine oxides, esters, sugar-based surfactants, polymericsurfactants, and mixtures thereof. Examples of alkoxylates are compoundssuch as alcohols, alkylphenols, amines, amides, arylphenols, fatty acidsor fatty acid esters which have been alkoxylated with 1 to 50equivalents. Ethylene oxide and/or propylene oxide may be employed forthe alkoxylation, preferably ethylene oxide. Examples of N-substitutedfatty acid amides are fatty acid glucamides or fatty acid alkanolamides.Examples of esters are fatty acid esters, glycerol esters ormonoglycerides. Examples of sugar-based surfactants are sorbitans,ethoxylated sorbitans, sucrose and glucose esters oralkylpolyglucosides. Examples of polymeric surfactants are home- orcopolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.

Suitable cationic surfactants are quaternary surfactants, for examplequaternary ammonium compounds with one or two hydrophobic groups, orsalts of long-chain primary amines. Suitable amphoteric surfactants arealkylbetains and imidazolines. Suitable block polymers are blockpolymers of the A-B or A-B-A type comprising blocks of polyethyleneoxide and polypropylene oxide, or of the A-B-C type comprising alkanol,polyethylene oxide and polypropylene oxide. Suitable polyelectrolytesare polyacids or polybases. Examples of polyacids are alkali salts ofpolyacrylic acid or polyacid comb polymers. Examples of polybases arepolyvinylamines or polyethyleneamines.

Suitable adjuvants are compounds, which have a neglectable or even nopesticidal activity themselves, and which improve the biologicalperformance of the compound I on the target. Examples are surfactants,mineral or vegetable oils, and other auxiliaries. Further examples arelisted by Knowles, Adjuvants and additives, Agrow Reports DS256, T&FInforma UK, 2006, chapter 5.

Suitable thickeners are polysaccharides (e.g. xanthan gum,carboxymethylcellulose), anorganic clays (organically modified orunmodified), polycarboxylates, and silicates. Suitable bactericides arebronopol and isothiazolinone derivatives such as alkylisothiazolinonesand benzisothiazolinones. Suitable anti-freezing agents are ethyleneglycol, propylene glycol, urea and glycerin.

Suitable anti-foaming agents are silicones, long chain alcohols, andsalts of fatty acids. Particularly preferred are silicone-basedanti-foaming agents such as polydimethylsiloxanes (e.g. SAG 1572 asavailable from Momentive, Silcolapse-481 or Silcolapse-482 from Elkem).Suitable silicone-based anti-foaming agents have also been described inWO2005/117590A2, Suitable colorants (e.g. in red, blue, or green) arepigments of low water solubility and water-soluble dyes. Examples areinorganic colorants (e.g. iron oxide, titan oxide, ironhexacyanoferrate) and organic colorants (e.g. alizarin-, azo- andphthalocyanine colorants). Suitable tackifiers or binders arepolyvinylpyrrolidons, polyvinylacetates, polyvinyl alcohols,polyacrylates, biological or synthetic waxes, and cellulose ethers.

Examples for composition types and their preparation are:

i) Water-Soluble Concentrates (SL, LS)

10-60 wt % of glufosinate or a salt thereof, 5-60 wt % of compound offormula (I) and 1-50 wt % of the amine component are dissolved in waterand/or in a water-soluble solvent (e.g. alcohols) ad 100 wt %.

ii) Dispersible Concentrates (DC)

5-25 wt % of glufosinate or a salt thereof, 5 to 60 wt % of compound offormula (I), 1-50 wt % of the amine component, and 1-10 wt % dispersant(e. g. polyvinylpyrrolidone) are dissolved in organic solvent (e.g.cyclohexanone) ad 100 wt %. Dilution with water gives a dispersion.

iii) Emulsifiable Concentrates (EC)

15-70 wt % of glufosinate or a salt thereof, 5-10 wt % emulsifiers (e.g.calcium dodecylbenzenesulfonate and castor oil ethoxylate), 5-60 wt % ofcompound of formula (I) and 1 to 50 wt % of the amine component aredissolved in water-insoluble organic solvent (e.g. aromatic hydrocarbon)ad 100 wt %. Dilution with water gives an emulsion.

iv) Emulsions (EW, EO, ES)

5-40 wt % of glufosinate or a salt thereof and 1-10 wt % emulsifiers(e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) 5-60 wt% of compound of formula (I) and 1-50 wt % of the amine component aredissolved in 20-40 wt % water-insoluble organic solvent (e.g. aromatichydrocarbon). This mixture is introduced into water ad 100 wt % by meansof an emulsifying machine and made into a homogeneous emulsion. Dilutionwith water gives an emulsion.

v) Suspensions (SC, OD, FS)

In an agitated ball mill, 20-60 wt % of glufosinate or a salt thereofare comminuted with addition of 2-10 wt % dispersants and wetting agents(e.g. sodium lignosulfonate and alcohol ethoxylate), 0, 1-2 wt %thickener (e.g. xanthan gum), 5-60 wt % of compound of formula (I), 1-50wt % of the amine component, and water ad 100 wt % to give a fine activesubstance suspension. Dilution with water gives a stable suspension ofthe active substance. For FS type composition up to 40 wt % binder (e.g.polyvinylalcohol) is added.

vi) Microemulsion (ME)

5-20 wt % of glufosinate or a salt thereof are added to 5-30 wt %organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone),10-25 wt % surfactant blend (e.g. alkohol ethoxylate and arylphenolethoxylate), 1-50 wt % of the amine component, and 5-60 wt % of thecompound of formula (I) and water ad 100%. This mixture is stirred for 1h to produce spontaneously a thermodynamically stable microemulsion.

vii) Microcapsules (CS)

An oil phase comprising 5-50 wt % of glufosinate or a salt thereof, 0-40wt % water insoluble organic solvent (e.g. aromatic hydrocarbon), 5-60wt % of compound of formula (I), 5-50 wt % of compound of formula (I),2-15 wt % acrylic monomers (e.g. methylmethacrylate, methacrylic acidand a di- or triacrylate) are dispersed into an aqueous solution of aprotective colloid (e.g. polyvinyl alcohol). Radical polymerizationinitiated by a radical initiator results in the formation ofpoly(meth)acrylate microcapsules. Alternatively, an oil phase comprising5-50 wt % of a glufosinate or a salt thereof, 0-40 wt % water insolubleorganic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer(e.g. diphenylmethene-4,4′-diisocyanatae) are dispersed into an aqueoussolution of a protective colloid (e.g. polyvinyl alcohol). The additionof a polyamine (e.g. hexamethylenediamine) results in the formation of apolyurea microcapsules. The microcapsules are added to an aqueouscomposition containing 1-50 wt % of the amine component. The monomersamount to 1-10 wt %. The wt % relate to the total CS composition.

The compositions types i) to vii) may optionally comprise furtherauxiliaries, such as 0.1-1 wt % bactericides, 5-15 wt % anti-freezingagents, 0.1-1 wt % anti-foaming agents, and 0.1-1 wt % colorants.

Solutions for seed treatment (LS), Suspoemulsions (SE), flowableconcentrates (FS), emulsions (ES), emulsifiable concentrates (EC) areusually employed for the purposes of treatment of plant propagationmaterials, particularly seeds. The compositions in question give, aftertwo-to-tenfold dilution, concentrations of glufosinate or a salt thereofof from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, inthe ready-to-use preparations. Application can be carried out before orduring sowing. Methods for applying the herbicidal composition, on toplant propagation material, especially seeds include dressing, coating,pelleting, dusting, soaking and in-furrow application methods of thepropagation material. Preferably, the herbicidal composition is appliedon to the plant propagation material by a method such that germinationis not induced, e. g. by seed dressing, pelleting, coating and dusting.

Exemplary formulation types of the herbicidal composition have beendescribed in WO2007/092351A1 and WO2005/117583A2.

Various types of oils, wetters, adjuvants, fertilizer, ormicronutrients, and further pesticides (e.g. herbicides, insecticides,fungicides, growth regulators, safeners) may be added to the herbicidalcomposition comprising them as premix or, if appropriate not untilimmediately prior to use (tank mix). These agents can be admixed withthe herbicidal compositions according to the invention in a weight ratioof 1:100 to 100:1, preferably 1:10 to 10:1.

The user applies the herbicidal composition according to the inventionusually from a pre-dosage device, a knapsack sprayer, a spray tank, aspray plane, or an irrigation system. Usually, the herbicidalcomposition is made up with water, buffer, and/or further auxiliaries tothe desired application concentration and the ready-to-use spray liquoror the herbicidal composition according to the invention is thusobtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, ofthe ready-to-use spray liquor are applied per hectare of agriculturaluseful area.

According to one embodiment, individual components of the herbicidalcomposition according to the invention such as parts of a kit or partsof a binary or ternary mixture may be mixed by the user himself in aspray tank and further auxiliaries may be added, if appropriate.

In a further embodiment, either individual components of the herbicidalcomposition according to the invention or partially premixed components,e. g. components comprising compounds of formula (I) and/or glufosinateor a salt thereof and/or the amine component may be mixed by the user ina spray tank and further auxiliaries and additives may be added, ifappropriate.

In a further embodiment, either individual components of the herbicidalcomposition according to the invention or partially premixed components,e. g. components comprising compounds of formula (I) and/or glufosinateor a salt thereof and/or the amine component can be applied jointly(e.g. after tank mix) or consecutively.

The herbicidal compositions have a comparatively low dynamic viscosityand stay homogeneous even at high concentrations of compound of formula(I).

The dynamic viscosity as referred to herein can be measured by means ofa Brookfield viscosimeter, i.e. a rotational viscosimeter with acone-plate geometry. The dynamic viscosity may be determined accordingto industry standard EN ISO 2555:2018. Usually, the dynamic viscosity ismeasured at 25° C. In this method, the shear rate of the rotationviscosimeter is constantly increased and the shear stress is measured.For Newtonian Fluids, the measurement results in a linear datasetaccording to a direct proportionality between the shear stress and theshear rate. For non-Newtonian fluids, the measurement results in anon-linear dependency between shear stress and shear rate. The dynamicviscosity, also called apparent viscosity, is typically determined bymeasuring the slope of a line through the origin of the coordinatesystem and the shear stress as determined at a shear rate of 100/second.The true viscosity, which may be different from the apparent viscosityfor non-Newtonian fluids, is determined by calculating the slope of thetangent of the experimental curve as measured at a shear rate of100/second.

The agrochemical composition usually has a true viscosity at 20° C. lessthan to 2000 mPas, preferably less than 1000 mPas, more preferably lessthan 500 mPas. The agrochemical composition usually has an apparentviscosity at 20° C. less than to 3000 mPas, preferably less than 1500mPas, more preferably less than 1000 mPas.

The herbicidal composition may contain a second agrochemical activeingredient. Typically, the second agrochemical active ingredient is apesticide, preferably selected from fungicides, insecticides,nematicides, herbicides, safeners, micronutrients, biopesticides,nitrification inhibitors, and/or growth regulators. In one embodiment,the second agrochemical active ingredient is an insecticide. In anotherembodiment, the second agrochemical active ingredient is a fungicide. Inyet another embodiment the second agrochemical active ingredient is aherbicide. The skilled worker is familiar with such pesticides, whichcan be found, for example, in the Pesticide Manual, 16th Ed. (2013), TheBritish Crop Protection Council, London. Suitable insecticides areinsecticides from the class of the carbamates, organophosphates,organochlorine insecticides, phenylpyrazoles, pyrethroids,neonicotinoids, spinosins, avermectins, milbemycins, juvenile hormoneanalogs, alkyl halides, organotin compounds nereistoxin analogs,benzoylureas, diacylhydrazines, and METI acarizides. Suitable fungicidesare fungicides from the classes of dinitroanilines, allylamines,anilinopyrimidines, antibiotics, aromatic hydrocarbons,benzenesulfonamides, benzimidazoles, benzisothiazoles, benzophenones,benzothiadiazoles, benzotriazines, benzyl carbamates, carbamates,carboxamides, carboxylic acid diamides, chloronitriles cyanoacetamideoximes, cyanoimidazoles, cyclopropanecarboxamides, dicarboximides,dihydrodioxazines, dinitrophenyl crotonates, dithiocarbamates,dithiolanes, ethylphosphonates, ethylaminothiazolecarboxamides,guanidines, hydroxy-(2-amino)pyrimidines, hydroxyanilides, imidazoles,imidazolinones, inorganic substances, isobenzofuranones,methoxyacrylates, methoxycarbamates, morpholines, N-phenylcarbamates,oxazolidinediones, oximinoacetates, oximinoacetamides,peptidylpyrimidine nucleosides, phenylacetamides, phenylamides,phenylpyrroles, phenylureas, phosphonates, phosphorothiolates,phthalamic acids, phthalimides, piperazines, piperidines, propionamides,pyridazinones, pyridines, pyridinylmethylbenzamides, pyrimidinamines,pyrimidines, pyrimidinonehydrazones, pyrroloquinolinones,quinazolinones, quinolines, quinones, sulfamides, sulfamoyltriazoles,thiazolecarboxamides, thiocarbamates, thiophanates,thiophenecarboxamides, toluamides, triphenyltin compounds, triazines,triazoles.

Suitable herbicides are herbicides from the classes of the acetamides,amides, aryloxyphenoxypropionates, benzamides, benzofuran, benzoicacids, benzothiadiazinones, bipyridylium, carbamates, chloroacetamides,chlorocarboxylic acids, cyclohexanediones, dinitroanilines,dinitrophenol, diphenyl ether, glycines, imidazolinones, isoxazoles,isoxazolidinones, nitriles, N-phenylphthalimides, oxadiazoles,oxazolidinediones, oxyacetamides, phenoxycarboxylic acids,phenylcarbamates, phenylpyrazoles, phenylpyrazolines, phenylpyridazines,phosphinic acids, phosphoroamidates, phosphorodithioates, phthalamates,pyrazoles, pyridazinones, pyridines, pyridinecarboxylic acids,pyridinecarboxamides, pyrimidinediones, pyrimidinyl(thio)benzoates,quinolinecarboxylic acids, semicarbazones,sulfonylaminocarbonyltriazolinones, sulfonylureas, tetrazolinones,thiadiazoles, thiocarbamates, triazines, triazinones, triazoles,triazolinones, triazolocarboxamides, triazolopyrimidines, triketones,uracils, ureas. Suitable plant growth regulators are antiauxins, auxins,cytokinins, defoliants, ethylene modulators, ethylene releasers,gibberellins, growth inhibitors, morphactins, growth retardants, growthstimulators, and further unclassified plant growth regulators. Suitablemicronutrients are compounds comprising boron, zinc, iron, copper,manganese, chlorine, and molybdenum.

The herbicidal composition may comprise the second agrochemical activeingredient in a concentration of at least 1 wt %, preferably at least 5wt % more preferably at least 10 wt %, most preferably at least 25 wt %,and in particular at least 30 wt % based on the total weight of theherbicidal composition. The herbicidal composition may comprise thesecond agrochemical active ingredient in a concentration of up to 90 wt%, preferably up to 70 wt %, more preferably up to 50 wt % based on thetotal weight of the herbicidal composition. The herbicidal compositionmay comprise the second agrochemical active ingredient in aconcentration of from 1 to 70 wt %, preferably 1 to 60 wt %, morepreferably 5 to 50 wt % based on the total weight of the composition.

Usually, the herbicidal composition contains glufosinate or a saltthereof, preferably the ammonium salt of glufosinate, and a secondagrochemical active ingredient selected from

B) herbicides of class b1) to b15):

-   -   b1) lipid biosynthesis inhibitors;    -   b2) acetolactate synthase inhibitors (ALS inhibitors);    -   b3) photosynthesis inhibitors;    -   b4) protoporphyrinogen-IX oxidase inhibitors (PPO inhibitor),    -   b5) bleacher herbicides;    -   b6) enolpyruvyl shikimate 3-phosphate synthase inhibitors (EPSP        inhibitors);    -   b7) glutamine synthetase inhibitors;    -   b8) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors);    -   b9) mitosis inhibitors;    -   b10) inhibitors of the synthesis of very long chain fatty acids        (VLCFA inhibitors);    -   b11) cellulose biosynthesis inhibitors;    -   b12) decoupler herbicides;    -   b13) auxinic herbicides;    -   b14) auxin transport inhibitors; and    -   b15) other herbicides selected from the group consisting of        bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin,        cumyluron, dalapon, dazomet, difenzoquat,        difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and        its salts, etobenzanid, flamprop, flamprop-isopropyl,        flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl,        flurenol, flurenol-butyl, flurprimidol, fosamine,        fosamine-ammonium, indanofan, indaziflam, maleic hydrazide,        mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide,        methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid,        oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine,        triaziflam, tridiphane and        6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (CAS        499223-49-3) and its salts and esters;        including their agriculturally acceptable salts or derivatives;        and        C) safeners.

If the herbicidal compounds B and/or the safeners C as described hereinare capable of forming geometrical isomers, for example E/Z isomers, itis possible to use both, the pure isomers and mixtures thereof, in theherbicidal composition according to the invention.

If the herbicidal compounds B and/or the safeners C as described hereinhave one or more centres of chirality and, as a consequence, are presentas enantiomers or diastereomers, it is possible to use both, the pureenantiomers and diastereomers and their mixtures, in the compositionsaccording to the invention.

If the herbicidal compounds B and/or the safeners C as described hereinhave ionizable functional groups, they can also be employed in the formof their agriculturally acceptable salts. Suitable are, in general, thesalts of those cations and the acid addition salts of those acids whosecations and anions, respectively, have no adverse effect on the activityof the active compounds.

Preferred cations are the ions of the alkali metals, preferably oflithium, sodium and potassium, of the alkaline earth metals, preferablyof calcium and magnesium, and of the transition metals, preferably ofmanganese, copper, zinc and iron, further ammonium and substitutedammonium in which one to four hydrogen atoms are replaced byC₁-C₄-alkyl, hydroxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl or benzyl, preferably ammonium,methylammonium, isopropylammonium, dimethylammonium, diethylammonium,diisopropylammonium, trimethylammonium, triethylammonium,tris(isopropyl)ammonium, heptylammonium, dodecylammonium,tetradecylammonium, tetramethylammonium, tetraethylammonium,tetrabutylammonium, 2-hydroxyethylammonium (olamine salt),2-(2-hydroxyeth-1-oxy)eth-1-ylammonium (diglycolamine salt),di(2-hydroxyeth-1-yl)ammonium (diolamine salt),tris(2-hydroxyethyl)ammonium (trolamine salt),tris(2-hydroxypropyl)ammonium, benzyltrimethylammonium,benzyltriethylammonium, N,N,N-trimethylethanolammonium (choline salt),furthermore phosphonium ions, sulfonium ions, preferablytri(C₁-C₄-alkyl)sulfonium, such as trimethylsulfonium, and sulfoxoniumions, preferably tri(C₁-C₄-alkyl)sulfoxonium, and finally the salts ofpolybasic amines such as N,N-bis-(3-aminopropyl)methylamine anddiethylenetriamine.

Anions of useful acid addition salts are primarily chloride, bromide,fluoride, iodide, hydrogensulfate, methylsulfate, sulfate,dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate,hexafluorosilicate, hexafluorophosphate, benzoate and also the anions ofC₁-C₄-alkanoic acids, preferably formate, acetate, propionate andbutyrate.

Herbicidal compounds B and/or safeners C as described herein having acarboxyl group can be employed in the form of the acid, in the form ofan agriculturally suitable salt as mentioned above or else in the formof an agriculturally acceptable derivative, for example as amides, suchas mono- and di-C₁-C₆-alkylamides or arylamides, as esters, for exampleas allyl esters, propargyl esters, C₁-C₁₀-alkyl esters, alkoxyalkylesters, tefuryl ((tetrahydrofuran-2-yl)methyl) esters and also asthioesters, for example as C₁-C₁₀-alkylthio esters. Preferred mono- anddi-C₁-C₅-alkylamides are the methyl and the dimethylamides. Preferredarylamides are, for example, the anilides and the 2-chloroanilides.Preferred alkyl esters are, for example, the methyl, ethyl, propyl,isopropyl, butyl, isobutyl, pentyl, mexyl (1-methylhexyl), meptyl(1-methylheptyl), heptyl, octyl or isooctyl (2-ethylhexyl) esters.Preferred C₁-C₄-alkoxy-C₁-C₄-alkyl esters are the straight-chain orbranched C₁-C₄-alkoxy ethyl esters, for example the 2-methoxyethyl,2-ethoxyethyl, 2-butoxyethyl (butotyl), 2-butoxypropyl or 3-butoxypropylester. An example of a straight-chain or branched C₁-C₁₀-alkylthio esteris the ethylthio ester.

According to a first embodiment of the invention, the herbicidalcomposition contains as second agrochemical active ingredient aninhibitor of the lipid biosynthesis (herbicide b1). These are compoundsthat inhibit lipid biosynthesis. Inhibition of the lipid biosynthesiscan be affected either through inhibition of acetylCoA carboxylase(hereinafter termed ACC herbicides) or through a different mode ofaction (hereinafter termed non-ACC herbicides). The ACC herbicidesbelong to the group A of the HRAC classification system whereas thenon-ACC herbicides belong to the group N of the HRAC classification.

According to a second embodiment of the invention the herbicidalcomposition contains as second agrochemical active ingredient an ALSinhibitor (herbicide b2). The herbicidal activity of these compounds isbased on the inhibition of acetolactate synthase and thus on theinhibition of the branched chain amino acid biosynthesis. Theseinhibitors belong to the group B of the HRAC classification system.

According to a third embodiment of the invention, the herbicidalcomposition contains as second agrochemical active ingredient aninhibitor of photosynthesis (herbicide b3). The herbicidal activity ofthese compounds is based either on the inhibition of the photosystem IIin plants (so-called PSII inhibitors, groups C1, C2 and C3 of HRACclassification) or on diverting the electron transfer in photosystem Iin plants (so-called PSI inhibitors, group D of HRAC classification) andthus on an inhibition of photosynthesis. Amongst these, PSII inhibitorsare preferred.

According to a fourth embodiment of the invention, the herbicidalcomposition contains as second agrochemical active ingredient aninhibitor of protoporphyrinogen-IX-oxidase (herbicide b4). Theherbicidal activity of these compounds is based on the inhibition of theprotoporphyrinogen-IX-oxidase. These inhibitors belong to the group E ofthe HRAC classification system.

According to a fifth embodiment of the invention, the herbicidalcomposition contains as second agrochemical active ingredient ableacher-herbicide (herbicide b5), preferably a HPPD inhibitor. Theherbicidal activity of these compounds is based on the inhibition of thecarotenoid biosynthesis. These include compounds which inhibitcarotenoid biosynthesis by inhibition of phytoene desaturase (so-calledPDS inhibitors, group F1 of HRAC classification), compounds that inhibitthe 4-hydroxyphenylpyruvate-dioxygenase (HPPD inhibitors, group F2 ofHRAC classification), compounds that inhibit DOXsynthase (group F4 ofHRAC class) and compounds which inhibit carotenoid biosynthesis by anunknown mode of action (bleacher—unknown target, group F3 of HRACclassification).

According to a sixth embodiment of the invention, the herbicidalcomposition contains as second agrochemical active ingredient an EPSPsynthase inhibitor (herbicide b6). The herbicidal activity of thesecompounds is based on the inhibition of enolpyruvyl shikimate3-phosphate synthase, and thus on the inhibition of the amino acidbiosynthesis in plants. These inhibitors belong to the group G of theHRAC classification system.

According to a seventh embodiment of the invention, the herbicidalcomposition contains as second agrochemical active ingredient aglutamine synthetase inhibitor (herbicide b7). The herbicidal activityof these compounds is based on the inhibition of glutamine synthetase,and thus on the inhibition of the amino acid biosynthesis in plants.These inhibitors belong to the group H of the HRAC classificationsystem.

According to an eighth embodiment of the invention, the herbicidalcomposition contains as second agrochemical active ingredient a DHPsynthase inhibitor (herbicide b8). The herbicidal activity of thesecompounds is based on the inhibition of 7,8-dihydropteroate synthase.These inhibitors belong to the group I of the HRAC classificationsystem.

According to a ninth embodiment of the invention, the herbicidalcomposition contains as second agrochemical active ingredient a mitosisinhibitor (herbicide b9). The herbicidal activity of these compounds isbased on the disturbance or inhibition of microtubule formation ororganization, and thus on the inhibition of mitosis. These inhibitorsbelong to the groups K1 and K2 of the HRAC classification system. Amongthese, compounds of the group K1, in particular dinitroanilines, arepreferred.

According to a tenth embodiment of the invention, the herbicidalcontains as second agrochemical active ingredient a VLCFA inhibitor(herbicide b10). The herbicidal activity of these compounds is based onthe inhibition of the synthesis of very long chain fatty acids and thuson the disturbance or inhibition of cell division in plants. Theseinhibitors belong to the group K3 of the HRAC classification system.

According to an eleventh embodiment of the invention, the herbicidalcontains as second agrochemical active ingredient a cellulosebiosynthesis inhibitor (herbicide b11). The herbicidal activity of thesecompounds is based on the inhibition of the biosynthesis of celluloseand thus on the inhibition of the synthesis of cell walls in plants.These inhibitors belong to the group L of the HRAC classificationsystem.

According to a twelfth embodiment of the invention, the herbicidalcontains as second agrochemical active ingredient a decoupler herbicide(herbicide b12). The herbicidal activity of these compounds is based onthe disruption of the cell membrane. These inhibitors belong to thegroup M of the HRAC classification system.

According to a thirteenth embodiment of the invention, the herbicidalcontains as second agrochemical active ingredient an auxinic herbicide(herbicide b13). These include compounds that mimic auxins, i.e. planthormones, and affect the growth of the plants. These compounds belong tothe group O of the HRAC classification system.

According to a fourteenth embodiment of the invention, the herbicidalcontains as second agrochemical active ingredient an auxin transportinhibitor (herbicide b14). The herbicidal activity of these compounds isbased on the inhibition of the auxin transport in plants. Thesecompounds belong to the group P of the HRAC classification system.

As to the given mechanisms of action and classification of the activesubstances, see e.g. “HRAC, Classification of Herbicides According toMode of Action”, http://www.plantprotection.org/hrac/MOA.html).

Examples of herbicides B which can be used as second agrochemical activeingredient in the herbicidal, according to the present invention are:

b1) from the group of the lipid biosynthesis inhibitors:ACC-herbicides such as alloxydim, alloxydim-sodium, butroxydim,clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop,cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop,fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop,fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop,haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden,profoxydim, propaquizafop, quizalofop, quizalofop-ethyl,quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl,quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim,4-(4′-Chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one(CAS 1312337-72-6);4-(2′,4′-Dichloro-4-cyclopropyl[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one(CAS 1312337-45-3);4-(4′-Chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one(CAS 1033757-93-5);4-(2′,4′-Dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione(CAS 1312340-84-3);5-(Acetyloxy)-4-(4′-chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one(CAS 1312337-48-6);5-(Acetyloxy)-4-(2′,4′-dichloro-4-cyclopropyl-[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one;5-(Acetyloxy)-4-(4′-chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one(CAS 1312340-82-1);5-(Acetyloxy)-4-(2′,4′-dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one(CAS 1033760-55-2);4-(4′-Chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester (CAS 1312337-51-1);4-(2′,4′-Dichloro-4-cyclopropyl-[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester;4-(4′-Chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester (CAS 1312340-83-2);4-(2′,4′-Dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester (CAS 1033760-58-5); and non ACC herbicidessuch as benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC,esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate,prosulfocarb, TCA, thio-bencarb, tiocarbazil, triallate and vernolate;b2) from the group of the ALS inhibitors:sulfonylureas such as amidosulfuron, azimsulfuron, bensulfuron,bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron,cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl,ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron,flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron,halosulfuron-methyl, imazosulfuron, iodosulfuron,iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium,mesosulfuron, met-azosulfuron, metsulfuron, metsulfuron-methyl,nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron,primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron,pyrazosulfuron-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl,sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron,tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron,triflusulfuron-methyl and tritosulfuron,imidazolinones such as imazamethabenz, imazamethabenz-methyl, imazamox,imazapic, imazapyr, imazaquin and imazethapyr, triazolopyrimidineherbicides and sulfonanilides such as cloransulam, cloransulam-methyl,diclosulam, flumetsulam, florasulam, metosulam, penoxsulam, pyrimisulfanand pyroxsulam,pyrimidinylbenzoates such as bispyribac, bispyribac-sodium,pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobac,pyrithiobac-sodium,4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoicacid-1-methylethyl ester (CAS 420138-41-6),4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoicacid propyl ester (CAS 420138-40-5),N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine(CAS 420138-01-8),sulfonylaminocarbonyl-triazolinone herbicides such as flucarbazone,flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium,thiencarbazone and thiencarbazone-methyl; and triafamone;b3) from the group of the photosynthesis inhibitors:amicarbazone, inhibitors of the photosystem II, e.g1-(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one(CAS 1654744-66-7),1-(5-tert-butylisoxazol-3-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one(CAS 1637455-12-9),1-(5-tert-butylisoxazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one(CAS 1637453-94-1),1-(5-tert-butyl-1-methyl-pyrazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one(CAS 1654057-29-0),1-(5-tert-butyl-1-methyl-pyrazol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrol-5-one(CAS 1654747-80-4),4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one;(CAS 2023785-78-4),4-hydroxy-1,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one(CAS 2023785-79-5),5-ethoxy-4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one(CAS 1701416-69-4),4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one(CAS 1708087-22-2),4-hydroxy-1,5-dimethyl-3-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]imidazolidin-2-one(CAS 2023785-80-8),1-(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2-one(CAS 1844836-64-1), triazine herbicides, including of chlorotriazine,triazinones, triazindiones, methylthiotriazines and pyridazinones suchas ametryn, atrazine, chloridazone, cyanazine, desmetryn, dimethametryn,hexazinone, metribuzin, prometon, prometryn, propazine, simazine,simetryn, terbumeton, terbuthylazin, terbutryn and trietazin, aryl ureasuch as chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron,fluometuron, isoproturon, isouron, linuron, metamitron,methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon,siduron, tebuthiuron and thiadiazuron, phenyl carbamates such asdesmedipham, karbutilat, phenmedipham, phenmedipham-ethyl, nitrileherbicides such as bromofenoxim, bromoxynil and its salts and esters,ioxynil and its salts and esters, uraciles such as bromacil, lenacil andterbacil, and bentazon and bentazon-sodium, pyridate, pyridafol,pentanochlor and propanil and inhibitors of the photosystem I such asdiquat, diquat-dibromide, paraquat, paraquat-dichloride andparaquat-dimetilsulfate.b4) from the group of the protoporphyrinogen-IX oxidase inhibitors:acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone,benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl,chlomethoxyfen, chlorphthalim, cinidon-ethyl, cyclopyranil, fluazolate,flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl,flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet,fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl,oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen,pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, tiafenacil,trifludimoxazin, ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate(CAS 353292-31-6; S-3100),N-ethyl-3-(2,6-dichloro-4-trifluoro-methylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(CAS 452098-92-9),N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(CAS 915396-43-9),N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(CAS 452099-05-7),N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoro-methylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(CAS 452100-03-7),3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione(CAS 451484-50-7),2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1,3-dione(CAS 1300118-96-0),1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione(CAS 1304113-05-0), methyl(E)-4-[2-chloro-5-[4-chloro-5-(difluoromethoxy)-1H-methyl-pyrazol-3-yl]-4-fluoro-phenoxy]-3-methoxy-but-2-enoate(CAS 948893-00-3), and3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione(CAS 212754-02-4),2-[2-chloro-5-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]-4-fluorophenoxy]-2-methoxy-aceticacid methyl ester (CAS 1970221-16-9),2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]-aceticacid methyl ester (CAS 2158274-96-3),2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]acetic acid ethyl ester (CAS 2158274-50-9), methyl2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]-4-fluoro-phenoxy]-2-pyridyl]oxy]acetate(CAS 2271389-22-9), ethyl2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]-4-fluoro-phenoxy]-2-pyridyl]oxy]acetate(CAS 2230679-62-4),2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]-aceticacid methyl ester (CAS 2158275-73-9),2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]acetic acid ethyl ester (CAS 2158274-56-5),2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]-N-(methylsulfonyl)-acetamide(CAS 2158274-53-2),2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]-N-(methylsulfonyl)-acetamide(CAS 2158276-22-1);b5) from the group of the bleacher herbicides:PDS inhibitors: beflubutamid, diflufenican, fluridone, flurochloridone,flurtamone, norflurazon, picolinafen, and4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS180608-33-7), HPPD inhibitors: benzobicyclon, benzofenap, bicyclopyrone,clomazone, fenquinotrione, isoxaflutole, mesotrione, oxotrione (CAS1486617-21-3), pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione,tefuryltrione, tembotrione, tolpyralate, topramezone, bleacher, unknowntarget: aclonifen, amitroleflumeturon,2-chloro-3-methylsulfanyl-N-(1-methyltetrazol-5-yl)-4-(trifluoromethyl)benzamide(CAS 1361139-71-0), bixlozone and2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (CAS81778-66-7);b6) from the group of the EPSP synthase inhibitors:glyphosate, glyphosate-isopropylammonium, glyphosate-potassium andglyphosate-trimesium (sulfosate);b7) from the group of the glutamine synthase inhibitors:bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-Pand glufosinate-ammonium;b8) from the group of the DHP synthase inhibitors:asulam;b9) from the group of the mitosis inhibitors:compounds of group K1: dinitroanilines such as benfluralin, butralin,dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin,prodiamine and trifluralin, phosphoramidates such as amiprophos,amiprophos-methyl, and butamiphos, benzoic acid herbicides such aschlorthal, chlorthal-dimethyl, pyridines such as dithiopyr andthiazopyr, benzamides such as propyzamide and tebutam; compounds ofgroup K2: carbetamide, chlorpropham, flamprop, flamprop-isopropyl,flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl and propham;among these, compounds of group K1, in particular dinitroanilines arepreferred;b10) from the group of the VLCFA inhibitors:chloroacetamides such as acetochlor, alachlor, amidochlor, butachlor,dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor,metolachlor-S, pethoxamid, pretilachlor, propachlor, propisochlor andthenylchlor, oxyacetanilides such as flufenacet and mefenacet,acetanilides such as diphenamid, naproanilide, napropamide andnapropamide-M, tetrazolinones such fentrazamide, and other herbicidessuch as anilofos, cafenstrole, fenoxasulfone, ipfencarbazone,piperophos, pyroxasulfone and isoxazoline compounds of the formulaeII.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9

the isoxazoline compounds of the formula (II) are known in the art, e.g.from WO2006/024820, WO2006/037945, WO2007/071900 and WO2007/096576;among the VLCFA inhibitors, preference is given to chloroacetamides andoxyacetamides;b11) from the group of the cellulose biosynthesis inhibitors:chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflamand 1-cyclohexyl-5-pentafluorphenyloxy-14-[1,2,4,6]thiatriazin-3-ylamine(CAS 175899-01-1);b12) from the group of the decoupler herbicides:dinoseb, dinoterb and DNOC and its salts;b13) from the group of the auxinic herbicides:2,4-D and its salts and esters such as clacyfos, 2,4-DB and its saltsand esters, aminocyclopyrachlor and its salts and esters, aminopyralidand its salts such as aminopyralid-dimethylammonium,aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin,benazolin-ethyl, chloramben and its salts and esters, clomeprop,clopyralid and its salts and esters, dicamba and its salts and esters,dichlorprop and its salts and esters, dichlorprop-P and its salts andesters, flopyrauxifen, fluroxypyr, fluroxypyr-butometyl,fluroxypyr-meptyl, halauxifen and its salts and esters (CAS943832-60-8); MCPA and its salts and esters, MCPA-thioethyl, MCPB andits salts and esters, mecoprop and its salts and esters, mecoprop-P andits salts and esters, picloram and its salts and esters, quinclorac,quinmerac, TBA (2,3,6) and its salts and esters, triclopyr and its saltsand esters, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661-72-9) and4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)picolinic acid (CAS1629965-65-6);b14) from the group of the auxin transport inhibitors: diflufenzopyr,diflufenzopyr-sodium, naptalam and naptalam-sodium;b15) from the group of the other herbicides: bromobutide, chlorflurenol,chlorflurenol-methyl, cinmethylin, cumyluron, cyclopyrimorate (CAS499223-49-3) and its salts and esters, dalapon, dazomet, difenzoquat,difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and itssalts, etobenzanid, flurenol, flurenol-butyl, flurprimidol, fosamine,fosamine-ammonium, indanofan, maleic hydrazide, mefluidide, metam,methiozolin (CAS 403640-27-7), methyl azide, methyl bromide,methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone,pelargonic acid, pyributicarb, quinoclamine and tridiphane.

In another embodiment of the present invention the second agrochemicalactive ingredient in the herbicidal composition is a safener C.

Safeners are chemical compounds which prevent or reduce damage on usefulplants without having a major impact on the herbicidal action of theherbicidal active components of the present compositions towardsunwanted plants. They can be applied either before sowings (e.g. on seedtreatments, shoots or seedlings) or in the pre-emergence application orpost-emergence application of the useful plant. The safeners and theherbicidal composition and/or the herbicides B can be appliedsimultaneously or in succession.

Suitable safeners are e.g. (quinolin-8-oxy)acetic acids,1-phenyl-5-haloalkyl-1H-1,2,4-triazol-3-carboxylic acids,1-phenyl-4,5-dihydro-5-alkyl-1H-pyrazol-3,5-dicarboxylic acids,4,5-dihydro-5,5-diaryl-3-isoxazol carboxylic acids, dichloroacetamides,alpha-oximinophenylacetonitriles, acetophenonoximes,4,6-dihalo-2-phenylpyrimidines,N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2-benzoic amides, 1,8-naphthalicanhydride, 2-halo-4-(haloalkyl)-5-thiazol carboxylic acids,phosphorthiolates and N-alkyl-O-phenylcarbamates and theiragriculturally acceptable salts and their agriculturally acceptablederivatives such amides, esters, and thioesters, provided they have anacid group.

Examples of preferred safeners C are benoxacor, cloquintocet,cyometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate,fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen,mefenpyr, mephenate, naphthalic anhydride, oxabetrinil,4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine(R-29148, CAS 52836-31-4), metcamifen and BPCMS (CAS 54091-06-4).

The active compounds B of groups b1) to b15) and the active compounds Care known herbicides and safeners, see, for example, The Compendium ofPesticide Common Names (http://www.alanwood.net/pesticides/); FarmChemicals Handbook 2000 volume 86, Meister Publishing Company, 2000; B.Hock, C. Fedtke, R. R. Schmidt, Herbizide [Herbicides], Georg ThiemeVerlag, Stuttgart 1995; W. H. Ahrens, Herbicide Handbook, 7th edition,Weed Science Society of America, 1994; and K. K. Hatzios, HerbicideHandbook, Supplement for the 7th edition, Weed Science Society ofAmerica, 1998. 2,2,5-Trimethyl-3-(dichloroacetyl)-1,3-oxazolidine [CASNo. 52836-31-4] is also referred to as R-29148.4-(Dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane [CAS No. 71526-07-3] isalso referred to as AD-67 and MON 4660.

The assignment of the active compounds to the respective mechanisms ofaction is based on current knowledge. If several mechanisms of actionapply to one active compound, this substance was only assigned to onemechanism of action.

Active compounds B and C having a carboxyl group can be employed in theform of the acid, in the form of an agriculturally suitable salt asmentioned above or else in the form of an agriculturally acceptablederivative in the compositions according to the invention.

In the case of dicamba, suitable salts include those, where thecounterion is an agriculturally acceptable cation. For example, suitablesalts of dicamba are dicamba-sodium, dicamba-potassium,dicamba-methylammonium, dicamba-dimethylammonium,dicamba-isopropylammonium, dicamba-diglycolamine, dicamba-olamine,dicamba-diolamine, dicamba-trolamine,dicamba-N,N-bis-(3-aminopropyl)methylamine anddicamba-diethylenetriamine. Examples of a suitable ester aredicamba-methyl and dicamba-butotyl.

Suitable salts of 2,4-D are 2,4-D-ammonium, 2,4-D-dimethylammonium,2,4-D-diethylammonium, 2,4-D-diethanolammonium (2,4-D-diolamine),2,4-D-triethanolammonium, 2,4-D-isopropylammonium,2,4-D-triisopropanolammonium, 2,4-D-heptylammonium,2,4-D-dodecylammonium, 2,4-D-tetradecylammonium, 2,4-D-triethylammonium,2,4-D-tris(2-hydroxypropyl)ammonium, 2,4-D-tris(isopropyl)ammonium,2,4-D-trolamine, 2,4-D-lithium, 2,4-D-sodium and2,4-D-N,N,N-trimethylethanolammonium (2,4-D choline). Examples ofsuitable esters of 2,4-D are 2,4-D-butotyl, 2,4-D-2-butoxypropyl,2,4-D-3-butoxypropyl, 2,4-D-butyl, 2,4-D-ethyl, 2,4-D-ethylhexyl,2,4-D-isobutyl, 2,4-D-isooctyl, 2,4-D-isopropyl, 2,4-D-meptyl,2,4-D-methyl, 2,4-D-octyl, 2,4-D-pentyl, 2,4-D-propyl, 2,4-D-tefuryl andclacyfos.

Suitable salts of 2,4-DB are for example 2,4-DB-sodium, 2,4-DB-potassiumand 2,4-DB-dimethylammonium. Suitable esters of 2,4-DB are for example2,4-DB-butyl and 2,4-DB-isoctyl. Suitable salts of dichlorprop are forexample dichlorprop-sodium, dichlorprop-potassium anddichlorprop-dimethylammonium. Examples of suitable esters of dichlorpropare dichlorprop-butotyl and dichlorprop-isoctyl.

Suitable salts and esters of MCPA include MCPA-butotyl, MCPA-butyl,MCPA-dimethylammonium, MCPA-diolamine, MCPA-ethyl, MCPA-thioethyl,MCPA-2-ethylhexyl, MCPA-isobutyl, MCPA-isoctyl, MCPA-isopropyl,MCPA-isopropylammonium, MCPA-methyl, MCPA-olamine, MCPA-potassium,MCPA-sodium and MCPA-trolamine.

A suitable salt of MCPB is MCPB sodium. A suitable ester of MCPB isMCPB-ethyl.Suitable salts of clopyralid are clopyralid-potassium,clopyralid-olamine and clopyralid-tris-(2-hydroxypropyl)ammonium.Example of suitable esters of clopyralid is clopyralid-methyl. Examplesof a suitable ester of fluroxypyr are fluroxypyr-meptyl andfluroxypyr-2-butoxy-1-methylethyl, wherein fluroxypyr-meptyl ispreferred.

Suitable salts of picloram are picloram-dimethylammonium,picloram-potassium, picloram-triisopropanolammonium,picloram-triisopropylammonium and picloram-trolamine. A suitable esterof picloram is picloram-isoctyl.

A suitable salt of triclopyr is triclopyr-triethylammonium. Suitableesters of triclopyr are for example triclopyr-ethyl andtriclopyr-butotyl.

Suitable salts and esters of chloramben include chloramben-ammonium,chloramben-diolamine, chloramben-methyl, chloramben-methylammonium andchloramben-sodium. Suitable salts and esters of 2,3,6-TBA include2,3,6-TBA-dimethylammonium, 2,3,6-TBA-lithium, 2,3,6-TBA-potassium and2,3,6-TBA-sodium.

Suitable salts and esters of aminopyralid includeaminopyralid-potassium, aminopyralid-dimethylammonium, andaminopyralid-tris(2-hydroxypropyl)ammonium.

Suitable salts of glyphosate are for example glyphosate-ammonium,glyphosate-diammonium, glyphosate-dimethylammonium,glyphosate-isopropylammonium, glyphosate-potassium, glyphosate-sodium,glyphosate-trimesium as well as the ethanolamine and diethanolaminesalts, preferably glyphosate-diammonium, glyphosate-isopropylammoniumand glyphosate-trimesium (sulfosate).

A suitable salt of glufosinate is for example glufosinate-ammonium. Asuitable salt of glufosinate-P is for example glufosinate-P-ammonium.

Suitable salts and esters of bromoxynil are for examplebromoxynil-butyrate, bromoxynil-heptanoate, bromoxynil-octanoate,bromoxynil-potassium and bromoxynil-sodium.

Suitable salts and esters of ioxonil are for example ioxonil-octanoate,ioxonil-potassium and ioxonil-sodium.

Suitable salts and esters of mecoprop include mecoprop-butotyl,mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-ethadyl,mecoprop-2-ethylhexyl, mecoprop-isoctyl, mecoprop-methyl,mecoprop-potassium, mecoprop-sodium and mecoprop-trolamine.

Suitable salts of mecoprop-P are for example mecoprop-P-butotyl,mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl,mecoprop-P-isobutyl, mecoprop-P-potassium and mecoprop-P-sodium.

A suitable salt of diflufenzopyr is for example diflufenzopyr-sodium.

A suitable salt of naptalam is for example naptalam-sodium.

Suitable salts and esters of aminocyclopyrachlor are for exampleaminocyclopyrachlor-dimethylammonium, aminocyclopyrachlor-methyl,aminocyclopyrachlor-triisopropanolammonium, aminocyclopyrachlor-sodiumand aminocyclopyrachlor-potassium.

A suitable salt of quinclorac is for examplequinclorac-dimethylammonium.

A suitable salt of quinmerac is for example quinmerac-dimethylammonium.

A suitable salt of imazamox is for example imazamox-ammonium.

Suitable salts of imazapic are for example imazapic-ammonium andimazapic-isopropylammonium.

Suitable salts of imazapyr are for example imazapyr-ammonium andimazapyr-isopropylammonium.

A suitable salt of imazaquin is for example imazaquin-ammonium.

Suitable salts of imazethapyr are for example imazethapyr-ammonium andimazethapyr-isopropylammonium.

A suitable salt of topramezone is for example topramezone-sodium.

Here and below, the term “binary herbicidal composition” refers toherbicidal compositions comprising glufosinate or a salt thereof,preferably L-glufosinate or a salt thereof, such as the ammonium salt ofglufosinate, and a herbicide B or a safener C.

In binary herbicidal compositions, the weight ratio of glufosinate or asalt thereof to active compound B is generally in the range of from1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, inparticular in the range of from 1:250 to 250:1 and particularlypreferably in the range of from 1:75 to 75:1.

In binary compositions comprising glufosinate or a salt thereof and asafener C, the weight ratio of glufosinate or a salt thereof to theactive compound C is generally in the range of from 1:1000 to 1000:1,preferably in the range of from 1:500 to 500:1, in particular in therange of from 1:250 to 250:1 and particularly preferably in the range offrom 1:75 to 75:1.

The herbicidal compositions are suitable as herbicides. Accordingly,these herbicidal compositions control vegetation on non-crop areas veryefficiently, especially at high rates of application. They act againstbroad-leafed weeds and grass weeds in crops such as wheat, rice, corn,soybeans and cotton without causing any significant damage to the cropplants. This effect is mainly observed at low rates of application.

The herbicidal compositions according to the invention are applied tothe plants mainly by spraying the leaves. Here, the application can becarried out using, for example, water as carrier by customary sprayingtechniques using spray liquor amounts of from about 100 to 1000 I/ha(for example from 300 to 400 I/ha). The herbicidal compositions may alsobe applied by the low-volume or the ultra-low-volume method, or in theform of microgranules.

Application of the herbicidal compositions according to the presentinvention can be done before, during and/or after, preferably duringand/or after, the emergence of the undesirable plants.

The herbicidal compositions according to the present invention can beapplied pre- or post-emergence or together with the seed of a cropplant. It is also possible to apply the herbicidal composition byapplying seed, pretreated with a herbicidal composition of theinvention, of a crop plant. If the active compounds are less welltolerated by certain crop plants, application techniques may be used inwhich the herbicidal compositions are sprayed, with the aid of thespraying equipment, in such a way that as far as possible they do notcome into contact with the leaves of the sensitive crop plants, whilethe active compounds reach the leaves of undesirable plants growingunderneath, or the bare soil surface (post-directed, lay-by).

In a further embodiment, the herbicidal composition according to theinvention can be applied by treating seed. The treatment of seedcomprises essentially all procedures familiar to the person skilled inthe art (seed dressing, seed coating, seed dusting, seed soaking, seedfilm coating, seed multilayer coating, seed encrusting, seed drippingand seed pelleting) based on the herbicidal compositions. Here, theherbicidal compositions can be applied diluted or undiluted. The term“seed” comprises seed of all types, such as, for example, corns, seeds,fruits, tubers, seedlings and similar forms. Here, preferably, the termseed describes corns and seeds. The seed used can be seed of the usefulplants mentioned above, but also the seed of transgenic plants or plantsobtained by customary breeding methods.

Moreover, it may be advantageous to apply the herbicidal compositions ofthe present invention on their own or jointly in combination with othercrop protection agents, for example with agents for controlling pests orphytopathogenic fungi or bacteria or with groups of active compoundswhich regulate growth. Also of interest is the miscibility with mineralsalt solutions which are employed for treating nutritional and traceelement deficiencies. Non-phytotoxic oils and oil concentrates can alsobe added.

When employed in plant protection, the amounts of glufosinate or saltthereof without formulation auxiliaries, are, depending on the kind ofeffect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kgper ha, more preferably from 0.05 to 0.9 kg per ha and in particularfrom 0.1 to 0.75 kg per ha.

In treatment of plant propagation materials such as seeds, e. g. bydusting, coating or drenching seed, amounts of glufosinate or saltthereof is of from 0.1 to 1000 g, preferably from 1 to 1000 g, morepreferably from 1 to 100 g and most preferably from 5 to 100 g, per 100kilogram of plant propagation material (preferably seeds) are generallyrequired.

When used in the protection of materials or stored products, the amountof glufosinate or salt thereof applied depends on the kind ofapplication area and on the desired effect. Amounts customarily appliedin the protection of materials are 0.001 g to 2 kg, preferably 0.005 gto 1 kg, of agrochemical active ingredient per cubic meter of treatedmaterial.

In the methods of the present invention it is immaterial whether theglufosinate or salt thereof, the compound of formula (I), the aminecomponent, and optionally the second agrochemical active ingredient areformulated and applied jointly or separately.

In the case of separate application it is of minor importance, in whichorder the application takes place. It is only necessary, that theglufosinate or salt thereof, the compound of formula (I), the aminecomponent, and optionally the second agrochemical active ingredient areapplied in a time frame that allows simultaneous action of the activeingredients on the plants, preferably within a time-frame of at most 14days, in particular at most 7 days.

Depending on the application method in question, the herbicidalcompositions according to the invention can additionally be employed ina further number of crop plants for eliminating undesirable pests, suchas invertebrate pests, fungi, or weeds, preferably weeds. Examples ofsuitable crops are the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis,Avena sativa, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa,Brassica napus var. napus, Brassica napus var. napobrassica, Brassicarapa var. silvestris, Brassica oleracea, Brassica nigra, Camelliasinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon,Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica),Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis,Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum,Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Heveabrasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglansregia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum,Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotianatabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus,Phaseolus vulgaris, Picea abies, Pinus spec., Pistacia vera, Pisumsativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca,Prunus cerasus, Prunus dulcis and prunus domestica, Ribes sylvestre,Ricinus communis, Saccharum officinarum, Secale cereale, Sinapis alba,Solanum tuberosum, Sorghum bicolor (S. vulgare), Theobroma cacao,Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Viciafaba, Vitis vinifera, Zea mays.

The herbicidal compositions according to the invention can also be usedin crops which have been modified by mutagenesis or genetic engineeringin order to provide a new trait to a plant or to modify an alreadypresent trait, preferably a resistance against glufosinate or its salts.

The term “crops” as used herein includes also (crop) plants which havebeen modified by mutagenesis or genetic engineering in order to providea new trait to a plant or to modify an already present trait.

Mutagenesis includes techniques of random mutagenesis using X-rays ormutagenic chemicals, but also techniques of targeted mutagenesis, inorder to create mutations at a specific locus of a plant genome.Targeted mutagenesis techniques frequently use oligonucleotides orproteins like CRISPR/Cas, zinc-finger nucleases, TALENs or meganucleasesto achieve the targeting effect.

Genetic engineering usually uses recombinant DNA techniques to createmodifications in a plant genome which under natural circumstances cannotreadily be obtained by cross breeding, mutagenesis or naturalrecombination. Typically, one or more genes are integrated into thegenome of a plant in order to add a trait or improve a trait. Theseintegrated genes are also referred to as transgenes in the art, whileplant comprising such transgenes are referred to as transgenic plants.The process of plant transformation usually produces severaltransformation events, which differ in the genomic locus in which atransgene has been integrated. Plants comprising a specific transgene ona specific genomic locus are usually described as comprising a specific“event”, which is referred to by a specific event name. Traits whichhave been introduced in plants or have been modified include inparticular herbicide tolerance, insect resistance, increased yield andtolerance to abiotic conditions, like drought.

Herbicide tolerance has been created by using mutagenesis as well asusing genetic engineering. Plants which have been rendered tolerant toacetolactate synthase (ALS) inhibitor herbicides by conventional methodsof mutagenesis and breeding comprise plant varieties commerciallyavailable under the name Clearfield®. However, most of the herbicidetolerance traits have been created via the use of transgenes.

Herbicide tolerance has been created to glyphosate, glufosinate, 2,4-D,dicamba, oxynil herbicides, like bromoxynil and ioxynil, sulfonylureaherbicides, ALS inhibitor herbicides and 4-hydroxyphenylpyruvatedioxygenase (HPPD) inhibitors, like isoxaflutole and mesotrione.

Transgenes which have been used to provide herbicide tolerance traitscomprise: for tolerance to glyphosate: cp4 epsps, epsps grg23ace5,mepsps, 2mepsps, gat4601, gat4621 and goxv247, for tolerance toglufosinate: pat and bar, for tolerance to 2,4-D: aad-1 and aad-12, fortolerance to dicamba: dmo, for tolerance to oxynil herbicies: bxn, fortolerance to sulfonylurea herbicides: zm-hra, csr1-2, gm-hra, S4-HrA,for tolerance to ALS inhibitor herbicides: csr1-2, for tolerance to HPPDinhibitor herbicides: hppdPF, W336 and avhppd-03.

Transgenic corn events comprising herbicide tolerance genes are forexample, but not excluding others, DAS40278, MON801, MON802, MON809,MON810, MON832, MON87411, MON87419, MON87427, MON88017, MON89034, NK603,GA21, MZHG0JG, HCEM485, VCO-Ø1981-5, 676, 678, 680, 33121, 4114, 59122,98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3, MS6, MZIR098, T25,TC1507 and TC6275.

Transgenic soybean events comprising herbicide tolerance genes are forexample, but not excluding others, GTS 40-3-2, MON87705, MON87708,MON87712, MON87769, MON89788, A2704-12, A2704-21, A5547-127, A5547-35,DP356043, DAS44406-6, DAS68416-4, DAS-81419-2, GU262, SYHTØH2, W62, W98,FG72 and CV127.

Transgenic cotton events comprising herbicide tolerance genes are forexample, but not excluding others, 19-51a, 31707, 42317, 81910,281-24-236, 3006-210-23, BXN10211, BXN10215, BXN10222, BXN10224,MON1445, MON1698, MON88701, MON88913, GHB119, GHB614, LLCotton25, T303-3and T304-40.

Transgenic canola events comprising herbicide tolerance genes are forexample, but not excluding others, MON88302, HCR-1, HCN10, HCN28, HCN92,MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2 and RF3.

Insect resistance has mainly been created by transferring bacterialgenes for insecticidal proteins to plants. Transgenes which have mostfrequently been used are toxin genes of Bacillus spec. and syntheticvariants thereof, like cry1A, cry1Ab, cry1Ab-Ac, cry1Ac, cry1A.105,cry1F, cry1Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1, cry34Ab1,cry35Ab1, cry9C, vip3A(a), vip3Aa20. However, also genes of plant originhave been transferred to other plants. In particular genes coding forprotease inhibitors, like CpTI and pinII. A further approach usestransgenes in order to produce double stranded RNA in plants to targetand downregulate insect genes. An example for such a transgene isdvsnf7.

Transgenic corn events comprising genes for insecticidal proteins ordouble stranded RNA are for example, but not excluding others, Bt10,Bt11, Bt176, MON801, MON802, MON809, MON810, MON863, MON87411, MON88017,MON89034, 33121, 4114, 5307, 59122, TC1507, TC6275, CBH-351, MIR162,DBT418 and MZIR098.

Transgenic soybean events comprising genes for insecticidal proteins arefor example, but not excluding others, MON87701, MON87751 and DAS-81419.

Transgenic cotton events comprising genes for insecticidal proteins arefor example, but not excluding others, SGK321, MON531, MON757, MON1076,MON15985, 31707, 31803, 31807, 31808, 42317, BNLA-601, Event1, COT67B,COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS 9124, 281-24-236,3006-210-23, GHB119 and SGK321.

Increased yield has been created by increasing ear biomass using thetransgene athb17, being present in corn event MON87403, or by enhancingphotosynthesis using the transgene bbx32, being present in the soybeanevent MON87712.

Crops comprising a modified oil content have been created by using thetransgenes: gm-fad2-1, Pj.D6D, Nc.Fad3, fad2-1A and fatb1-A. Soybeanevents comprising at least one of these genes are: 260-05, MON87705 andMON87769.

Tolerance to abiotic conditions, in particular to tolerance to drought,has been created by using the transgene cspB, comprised by the cornevent MON87460 and by using the transgene Hahb-4, comprised by soybeanevent IND-00410-5.

Traits are frequently combined by combining genes in a transformationevent or by combining different events during the breeding process.Preferred combination of traits are herbicide tolerance to differentgroups of herbicides, insect tolerance to different kind of insects, inparticular tolerance to lepidopteran and coleopteran insects, herbicidetolerance with one or several types of insect resistance, herbicidetolerance with increased yield as well as a combination of herbicidetolerance and tolerance to abiotic conditions.

Plants comprising singular or stacked traits as well as the genes andevents providing these traits are well known in the art. For example,detailed information as to the mutagenized or integrated genes and therespective events are available from websites of the organizations“International Service for the Acquisition of Agri-biotech Applications(ISAAA)” (http://www.isaaa.org/gmapprovaldatabase) and the “Center forEnvironmental Risk Assessment (CERA)”(http://cera-gmc.org/GMCropDatabase), as well as in patent applications,like EP3028573 and WO2017/011288.

The use of herbicidal compositions according to the invention on cropsmay result in effects which are specific to a crop comprising a certaingene or event. These effects might involve changes in growth behavior orchanged resistance to biotic or abiotic stress factors. Such effects mayin particular comprise enhanced yield, enhanced resistance or toleranceto insects, nematodes, fungal, bacterial, Mycoplasma, viral or viroidpathogens as well as early vigour, early or delayed ripening, cold orheat tolerance as well as changed amino acid or fatty acid spectrum orcontent.

Furthermore, plants are also covered that contain by the use ofrecombinant DNA techniques a modified amount of ingredients or newingredients, specifically to improve raw material production, e.g.,potatoes that produce increased amounts of amylopectin (e.g. Amflora®potato, BASF SE, Germany).

Furthermore, it has been found that the herbicidal compositionsaccording to the invention are also suitable for the defoliation and/ordesiccation of plant parts, for which crop plants such as cotton,potato, oilseed rape, sunflower, soybean or field beans, in particularcotton, are suitable.

In this regard herbicidal compositions have been found for thedesiccation and/or defoliation of plants, processes for preparing thesecompositions, and methods for desiccating and/or defoliating plantsusing the herbicidal compositions according to the invention.

As desiccants, herbicidal compositions according to the invention aresuitable in particular for desiccating the above-ground parts of cropplants such as potato, oilseed rape, sunflower and soybean, but alsocereals. This makes possible the fully mechanical harvesting of theseimportant crop plants.

Also of economic interest is the facilitation of harvesting, which ismade possible by concentrating within a certain period of time thedehiscence, or reduction of adhesion to the tree, in Citrus fruit,olives and other species and varieties of pomaceous fruit, stone fruitand nuts. The same mechanism, i.e. the promotion of the development ofabscission tissue between fruit part or leaf part and shoot part of theplants is also essential for the controlled defoliation of usefulplants, in particular cotton.

Moreover, a shortening of the time interval in which the individualcotton plants mature leads to an increased fiber quality afterharvesting.

The herbicidal composition may be applied in or on permanent cropland,or on permanent crops.

A permanent crop is one produced from plants which last for manyseasons, rather than being re-planted after each harvest. Permanentcrops are grown on permanent crop land in the form of agricultural landthat includes grasslands and shrublands, e.g. used to grow grape vinesor coffee; orchards used to grow fruit or olives; and forestedplantations, e.g. used to grow nuts or rubber. It does not include,however, tree farms intended to be used for wood or timber.

Preferred permanent croplands in the context of the present inventionare plantations, grasslands and shrublands. Preferably, the permanentcrops in the context of the present invention are plantation crops, andpreferably are selected from the group consisting fruit crops andorchard crops (preferably fruit trees, Citrus trees, mango trees, olivetrees, grape vines, coffee, cocoa, tea, and berries (such asstrawberries, raspberries, blueberries and currants)), Musaceae sp.crops (for example banana or plantain crops), nut trees (preferablyalmond trees, walnut trees, pistachio trees, pecan trees, hazelnuttrees), oil palm trees, rubber trees, sugarcane and cotton.

More preferably, the permanent crops are fruit trees (preferably pomefruit trees and stone fruit trees; preferred fruit trees are appletrees, pear trees, apricot trees, plum trees, cherry trees, peachtrees), olive trees, grape vines, coffee, tea), Musaceae sp. crops(preferably banana crops or plantain crops), nut trees (preferablyalmond trees, walnut trees, pistachio trees, pecan trees, hazelnuttrees), oil palm trees, rubber trees, and Citrus crops (preferablylemon, orange or grapefruit crops). Even more preferably, the permanentcrops are selected from the group consisting of apple trees, pear trees,apricot trees, plum trees, cherry trees, peach trees, olive trees, grapevines, coffee, tea, banana crops, nut trees (preferably almond trees,walnut trees, pistachio trees), oil palm trees, rubber trees, and Citruscrops (preferably lemon, orange or grapefruit crops). Particularlypreferably, the permanent crops are selected from the group consistingof apple trees, pear trees, apricot trees, plum trees, cherry trees,peach trees, olive trees, grape vines, coffee, tea, banana crops, almondtrees, walnut trees, oil palm trees, rubber trees, lemon crops, orangecrops and grapefruit crops The herbicidal composition may also beapplied on row crops and as well on specialty crops.

Row crops can be planted in rows wide enough to allow it to be tilled orotherwise cultivated by agricultural machinery, machinery tailored forthe seasonal activities of row crops. The particularity of row crops isthat they are planted and cultivated on a seasonal or yearly basis.Therefore, such crops yield products and profit relatively quickly andpredictably. A row crop is one produced from plants which last for manyseasons, rather than being re-planted after each harvest. Examples ofrow crops include soybeans, corn, canola, cotton, cereals or rice, butas well sunflower, potato, dry bean, field pea, flax, safflower,buckwheat and sugar beets.

Specialty crops are to be understood as fruits, vegetables or otherspecialty or plantation permanent crops such as trees, nuts, vines,(dried) fruits, ornamentals, oil palm, banana, rubber and the like,Horticulture and nursery crops, including floriculture, may also fallunder the definition of specialty crops. Vegetable crops includes forexample aubergine, beans, bell pepper, cabbage, chili, cucumber,eggplant, lettuce, melon, onion, potato, sweet potato, spinach andtomato. Plants being considered specialty crops are in generalintensively cultivated. For weed control in vegetable crops, it may bedesirable to shield the crops from contact with the spray solution thatcontains the herbicidal mixture according to the present invention.

In general, the crops which may be treated, may be of conventionalorigin or may be herbicide tolerant crops, preferably glufosinatetolerant crops. The herbicidal composition shows high herbicidal effectsalso against select crop plants, such as barley and soybean. This effectcan be used to control crop plants in crop rotation methods ofpreviously grown crop cultures. Typically, residual crop plants fromprevious rotation cycles remain after harvest and continue to growwithin the subsequently grown crop variety. This reduces the yield sincethe crop plants of two different crop rotation cycles compete on thesame locus of growth. The herbicidal composition may thus be applied tocontrol residual crop plants from previous crop rotation cycles to allowfor a homogeneous coverage with the subsequent crop plant.

In a preferred embodiment, the herbicidal composition is applied once,twice or three times per Gregorian calendar year, i.e. in oneapplication, in two applications or in three applications per yearaccording to the Gregorian calendar. In a preferred embodiment, theherbicidal composition is applied twice per Gregorian calendar year,i.e. in two applications per year according to the Gregorian calendar.In an alternatively preferred embodiment, the herbicidal composition isapplied one time per Gregorian calendar year, i.e. in one applicationper year according to the Gregorian calendar. In a preferred embodiment,the herbicidal composition is applied one time in about 12 months, i.e.in one application in about 12 months. In an alternative preferredembodiment, the herbicidal composition is applied between one and tentimes per Gregorian calendar year, i.e. in up to ten applications peryear according to the Gregorian calendar. This alternative preferredmethod is of particular usefulness in permanent crops, in particularthose grown under tropical conditions; in which case weeds growvigorously at any time of the year, and herbicide applications are to bere-peated as soon as the previous treatment loses its effectiveness andweeds start to regrow.

The herbicidal compositions are preferably used in post-emergenceapplications.

The invention includes the use and methods of application of theherbicidal composition for controlling undesirable vegetation in cropsin a burndown program, wherein the crop is produced by geneticengineering or by breeding, are tolerant to one or more herbicidesand/or resistant to pathogens such as plant-pathogenous fungi, and/or toattack by insects; preferably tolerant to glufosinate.

Preferred are crops, which are tolerant to glufosinate, wherein theglufosinate tolerant crop plant is preferably selected from the groupconsisting of rice, canola, soybean, corn and cotton plants.

Transgenic corn events comprising glufosinate tolerance genes are forexample, but not excluding others, 5307 x MIR604 x Bt11 x TC1507 x GA21x MIR162 (event code: SYN-Ø53Ø7-1 x SYN-IR6Ø4-5 x SYN-BTØ11-1 xDAS-Ø15Ø7-1 x MON-ØØØ21-9 x SYN-IR162-4, gene: pat, e.g. commerciallyavailable as Agrisure® Duracade™ 5222), 59122 (event code: DAS-59122-7,gene: pat, e.g. commercially available as Herculex™ RW), 5307 x MIR604 xBt11 x TC1507 x GA21 (event code: SYN-Ø53Ø7-1 x SYN-IR6Ø4-5 xSYN-BTØ11-1 x DAS-Ø15Ø7-1 x MON-ØØØ21-9, gene: pat, e.g. commerciallyavailable as Agrisure® Duracade™ 5122), 59122 x NK603 (event code:DAS-59122-7 x MON-ØØ6Ø3-6, gene: pat, e.g. commercially available asHerculex™ RW Roundup Ready™ 2), Bt10 (gene: pat, e.g. commerciallyavailable as Bt10), Bt11 (X4334CBR, X4734CBR) (event code: SYN-BTØ11-1,gene: pat, e.g. commercially available as Agrisure™ CB/LL), BT11 x 59122x MIR604 x TC1507 x GA21 (event code: SYN-BTØ11-1 x DAS-59122-7 xSYN-IR6Ø4-5 x DAS-Ø15Ø7-1 x MON-ØØØ21-9, gene: pat, e.g. commerciallyavailable as Agrisure® 3122), Bt11 x GA21 (event code: SYN-BTØ11-1 xMON-ØØØ21-9, gene: pat, e.g. commercially available as Agrisure™GT/CB/LL), Bt11 x MIR162 (event code: SYN-BTØ11-1 x SYN-IR162-4, gene:pat, e.g. commercially available as Agrisure® Viptera™ 2100), Bt11 xMIR162 x GA21 (event code: SYN-BTØ11-1 x SYN-IR162-4 x MON-ØØØ21-9,gene: pat, e.g. commercially available as Agrisure® Viptera™ 3110), BT11x MIR162 x MIR604 (event code: SYN-BTØ11-1 x SYN-IR162-4 x SYN-IR6Ø4-5,gene: pat, e.g. commercially available as Agrisure® Viptera™ 3100), Bt11x MIR162 x MIR604 x GA21 (event code: SYN-BTØ11-1 x SYN-IR162-4 xSYN-IR6Ø4-5 x MON-ØØØ21-9, gene: pat, e.g. commercially available asAgrisure® Viptera™ 3111, Agrisure® Viptera™ 4), Bt11 x MIR162 x TC1507 xGA21 (event code: SYN-BTØ11-1 x SYN-IR162-4 x DAS-Ø15Ø7-1 x MON-ØØØ21-9,gene: pat, e.g. commercially available as Agrisure™ Viptera 3220), Bt11x MIR604 (event code: SYN-BTØ11-1 x SYN-IR6Ø4-5, gene: pat, e.g.commercially available as Agrisure™ CB/LL/RW), BT11 x MIR604 x GA21(event code: SYN-BTØ11-1 x SYN-IR6Ø4-5 x MON-ØØØ21-9, gene: pat, e.g.commercially available as Agrisure™ 3000GT), Bt176 (176) (event code:SYN-EV176-9, gene: bar, e.g. commercially available as NaturGardKnockOut™, Maximizer™), CBH-351 (event code: ACS-ZMØØ4-3, gene: bar,e.g. commercially available as Star-link™ Maize), DBT418 (event code:DKB-89614-9, gene: bar, e.g. commercially available as Bt Xtra™ Maize),MON89034 x TC1507 x MON88017 x 59122 (event code: MON-89Ø34-3 xDAS-Ø15Ø7-1 x MON-88Ø17-3 x DAS-59122-7, gene: pat, e.g. commerciallyavailable as Genuity® SmartStax™), MON89034 x TC1507 x NK603 (eventcode: MON-89Ø34-3 x DAS-Ø15Ø7-1 x MON-ØØ6Ø3-6, gene: pat, e.g.commercially available as Power Core™), NK603 x T25 (event code:MON-ØØ6Ø3-6 x ACS-ZMØØ3-2, gene: pat, e.g. commercially available asRoundup Ready™ Liberty Link™ Maize), T14 (event code: ACS-ZMØØ2-1, gene:pat, e.g. commercially available as Liberty Link™ Maize), T25 (eventcode: ACS-ZMØØ3-2, gene: pat, e.g. commercially available as LibertyLink™ Maize), T25 x MON810 (event code: ACS-ZMØØ3-2 x MON-ØØ81Ø-6, gene:pat, e.g. commercially available as Liberty Link™ Yieldgard™ Maize),TC1507 (event code: DAS-Ø15Ø7-1, gene: pat, e.g. commercially availableas Herculex™ I, Herculex™ CB), TC1507 x 59122 x MON810 x MIR604 x NK603(event code: DAS-Ø15Ø7-1 x DAS-59122-7 x MON-ØØ81Ø-6 x SYN-IR6Ø4-5 xMON-ØØ6Ø3, gene: pat, e.g. commercially available as Optimum™ IntrasectXtreme), TC1507 x 59122 (event code: DAS-Ø15Ø7-1 x DAS-59122-7, gene:pat, e.g. commercially available as Herculex XTRA™), TC1507 x 59122 xMON810 x NK603 (event code: DAS-Ø15Ø7-1 x DAS-59122-7 x MON-ØØ81Ø-6 xMON-ØØ6Ø3-6, gene: pat, e.g. commercially available as Optimum™Intrasect XTRA), TC1507 x 59122 x NK603 (event code: DAS-Ø15Ø7-1 xDAS-59122-7 x MON-ØØ6Ø3-6, gene: pat, e.g. commercially available asHerculex XTRA™ RR), TC1507 x MIR604 x NK603 (event code: DAS-Ø15Ø7-1 xSYN-IR6Ø4-5 x MON-ØØ6Ø3-6, gene: pat, e.g. commercially available asOptimum™ TRIsect), TC1507 x MON810 x NK603 (event code: DAS-Ø15Ø7-1 xMON-ØØ81Ø-6 x MON-ØØ6Ø3-6, gene: pat, e.g. commercially available asOptimum™ Intrasect), TC1507 x NK603 (event code: DAS-Ø15Ø7-1 xMON-ØØ6Ø3-6, gene: pat, e.g. commercially available as Herculex™ I RR),3272 x Bt11 (event code: SYN-E3272-5 x SYN-BTØ11-1 gene: pat), 3272 xBt11 x GA21 (event code: SYN-E3272-5 x SYN-BTØ11-1 x MON-ØØØ21-9, gene:pat), 3272 x Bt11 x MIR604 (event code: SYN-E3272-5 x SYN-BTØ11-1 xSYN-IR6Ø4-5, gene: pat), 3272 x BT11 x MIR604 x GA21 (event code:SYN-E3272-5 x SYN-BTØ11-1 x SYN-IR6Ø4-5 x MON-ØØØ21-9, gene: pat), 33121(event code: DP-Ø33121-3, gene: pat), 4114 (event code: DP-ØØ4114-3,gene: pat), 59122 x GA21 (event code: DAS-59122-7 x MON-ØØØ21-9, gene:pat), 59122 x MIR604 (event code: DAS-59122-7 x SYN-IR6Ø4-5, gene: pat),5307 x MIR604 x Bt11 x TC1507 x GA21 x MIR162 (event code: gene: pat),59122 x MIR604 x GA21 (event code: DAS-59122-7 x SYN-IR6Ø4-5 xMON-ØØØ21-9, gene: pat), 59122 x MIR604 x TC1507 (event code:DAS-59122-7 x SYN-IR6Ø4-5 x DAS-Ø15Ø7-1, gene: pat), 59122 x MIR604 xTC1507 x GA21 (event code: gene: pat), (event code: DAS-59122-7 xSYN-IR6Ø4-5 x DAS-Ø15Ø7-1 x MON-ØØØ21-9, gene: pat), 59122 x MON810(event code: DAS-59122-7 x MON-ØØ81Ø-6, gene: pat), 59122 x MON810 xNK603 (event code: DAS-59122-7 x MON-ØØ81Ø-6 x MON-ØØ6Ø3-6, gene: pat),59122 x TC1507 x GA21 (event code: DAS-59122-7 x DAS-Ø15Ø7-1 xMON-ØØØ21-9, gene: pat), 676 (event code: PH-ØØØ676-7, gene: pat), 678(event code: PH-ØØØ678-9, gene: pat), 680 (event code: PH-ØØØ68Ø-2,gene: pat), 98140 x 59122 (event code: DP-Ø9814Ø-6 x DAS-59122-7, gene:pat), 98140 x TC1507 (event code: DP-Ø9814Ø-6 x DAS-Ø15Ø7-1, gene: pat),98140 x TC1507 x 59122 (event code: DP-Ø9814Ø-6 x DAS-Ø15Ø7-1 xDAS-59122-7, gene: pat), 59122 x MON88017 (event code: DAS-59122-7 xMON-88Ø17-3, gene: pat), Bt11 x 59122 (event code: SYN-BTØ11-1 xDAS-59122-7, gene: pat), Bt11 x 59122 x GA21 (event code: SYN-BTØ11-1 xDAS-59122-7 x MON-ØØØ21-9, gene: pat), Bt11 x 59122 x MIR604 (eventcode: SYN-BTØ11-1 x DAS-59122-7 x SYN-IR6Ø4-5, gene: pat), Bt11 x 59122x MIR604 x GA21 (event code: SYN-BTØ11-1 x DAS-59122-7 x SYN-IR6Ø4-5 xMON-ØØØ21-9, gene: pat), Bt11 x 59122 x MIR604 x TC1507 (event code:Bt11 x 59122 x MIR604 x TC1507, gene: pat), Bt11 x 59122 x TC1507 (eventcode: SYN-BTØ11-1 x DAS-59122-7 x DAS-Ø15Ø7-1, gene: pat), Bt11 x 59122x TC1507 x GA21 (event code: SYN-BTØ11-1 x DAS-59122-7 x DAS-Ø15Ø7-1 xMON-ØØØ21-9, gene: pat), Bt11 x MIR162 x TC1507 (event code: SYN-BTØ11-1x SYN-IR162-4 x DAS-Ø15Ø7-1, gene: pat), Bt11 x MIR604 x TC1507 (eventcode: SYN-BTØ11-1 x SYN-IR6Ø4-5 x DAS-Ø15Ø7-1, gene: pat), Bt11 x TC1507(event code: SYN-BTØ11-1 x DAS-Ø15Ø7-1, gene: pat), Bt11 x TC1507 x GA21(event code: SYN-BTØ11-1 x DAS-Ø15Ø7-1 x MON-ØØØ21-9, gene: pat), GA21 xT25 (event code: MON-ØØØ21-9 x ACS-ZMØØ3-2, gene: pat), MIR162 x TC1507(event code: SYN-IR162-4 x DAS-Ø15Ø7-1, gene: pat), MIR162 x TC1507 xGA21 (event code: SYN-IR162-4 x DAS-Ø15Ø7-1 x MON-ØØØ21-9, gene: pat),MIR604 x TC1507 (event code: SYN-IR6Ø4-5 x DAS-Ø15Ø7-1, gene: pat),MON87427 x MON89034 x TC1507 x MON88017 x 59122 (event code: MON-87427-7x MON-89Ø34-3 x DAS-Ø15Ø7-1 x MON-88Ø17-3 x DAS-59122-7, gene: pat),MON89034 x 59122 (event code: MON-89Ø34-3 x DAS-59122-7, gene: pat),MON89034 x 59122 x MON88017 (event code: gene: pat), MON89034 x TC1507(event code: MON-89Ø34-3 x DAS-59122-7 x MON-88Ø17-3, gene: pat), (eventcode: MON-89Ø34-3 x DAS-Ø15Ø7-1, gene: pat), MIR604 x TC1507 (eventcode: SYN-IR6Ø4-5 x DAS-Ø15Ø7-1, gene: pat), MON87427 x MON89034 xTC1507 x MON88Ø17 x 59122 (event code: MON-87427-7 x MON-89Ø34-3 xDAS-Ø15Ø7-1 x MON-88Ø17-3 x DAS-59122-7, gene: pat), MON89034 x 59122(event code: MON-89Ø34-3 x DAS-59122-7, gene: pat), MON89Ø34 x 59122 xMON88017 (event code: gene: pat), MON89034 x TC1507 (event code:MON-89Ø34-3 x DAS-59122-7 x MON-88Ø17-3, gene: pat), (event code:MON-89Ø34-3 x DAS-Ø15Ø7-1, gene: pat), DLL25 (B16) (event code:DKB-8979Ø-5, gene: bar), MIR604 x TC1507 (event code: SYN-IR6Ø4-5 xDAS-Ø15Ø7-1, gene: pat), MON87427 x MON89Ø34 x TC15Ø7 x MON88Ø17 x 59122(event code: MON-87427-7 x MON-89Ø34-3 x DAS-Ø15Ø7-1 x MON-88Ø17-3 xDAS-59122-7, gene: pat), MON89034 x 59122 (event code: MON-89Ø34-3 xDAS-59122-7, gene: pat), MON89034 x 59122 x MON88017 (event code:MON-89Ø34-3 x DAS-59122-7 x MON-88Ø17-3, gene: pat), MON89034 x TC1507(event code: MON-89Ø34-3 x DAS-Ø15Ø7-1, gene: pat), MON89034 x TC1507 x59122 (event code: MON-89Ø34-3 x DAS-Ø15Ø7-1 x DAS-59122-7, gene: pat),MON89034 x TC1507 x MON88017 (event code: MON-89Ø34-3 x DAS-Ø15Ø7-1 xMON-88Ø17-3, gene: pat), MON89034 x TC1507 x MON88017 x 59122 x DAS40278(event code: MON-89Ø34-3 x DAS-Ø15Ø7-1 x MON-88Ø17-3 x DAS-59122-7 xDAS-4Ø278-9, gene: pat), MON89034 x TC1507 x MON88017 x DAS40278 (eventcode: MON-89Ø34-3 x DAS-Ø15Ø7-1 x MON-88Ø17-3 x DAS-59122-7 xDAS-4Ø278-9, gene: pat), MON89034 x TC1507 x NK603 x DAS40278 (eventcode: MON-89Ø34-3 x DAS-Ø15Ø7-1 x MON-ØØ6Ø3-6 x DAS-4Ø278-9, gene: pat),NK603 x MON810 x 4114 x MIR 604 (event code: MON-00603-6 x MON-00810-6 xDP004114-3 x SYN-IR604-4, gene: pat), TC1507 x MON810 x MIR604 x NK603(event code: DAS-Ø15Ø7-1 x MON-ØØ81Ø-6 x SYN-IR6Ø4-5 x MON-ØØ6Ø3-6,gene: pat), TC1507 x 59122 x MON810 (event code: DAS-Ø15Ø7-1 xDAS-59122-7 x MON-ØØ81Ø-6, gene: pat), TC1507 x 59122 x MON88017 (eventcode: DAS-Ø15Ø7-1 x DAS-59122-7 x MON-88Ø17-3, gene: pat), TC1507 x GA21(event code: DAS-Ø15Ø7-1 x MON-ØØØ21-9, gene: pat), TC1507 x MON810(event code: DAS-Ø15Ø7-1 x MON-ØØ81Ø-6, gene: pat), TC1507 x MON810 xMIR162 x NK603 (event code: DAS-Ø15Ø7-1 x MON-ØØ81Ø-6 x SYN-IR162-4 xMON-ØØ6Ø3-6, gene: pat), 3272 x Bt11 x MIR604 x TC1507 x 5307 x GA21(event code: SYN-E3272-5 x SYN-BTØ11-1 x SYN-IR6Ø4-5 x DAS-Ø15Ø7-1 xSYN-Ø53Ø7-1 x MON-ØØØ21-9, gene: pat), TC1507 x MIR162 x NK603 (eventcode: DAS-Ø15Ø7-1 x SYN-IR162-4 x MON-ØØ6Ø3-6, gene: pat), TC1507 xMON810 x MIR162 (event code: DAS-Ø15Ø7-1 x MON-ØØ81Ø-6 x SYN-IR162-4,gene: pat), MON87419 (event code: MON87419-8, gene: pat), TC1507 xMON88017 (event code: DAS-Ø15Ø7-1 x MON-88Ø17-3, gene: pat), TC6275(event code: DAS-Ø6275-8, gene: bar), MZHG0JG (event code: SYN-ØØØJG-2,gene: pat), MZIR098 (event code: SYN-ØØØ98-3, gene: pat), Bt11 x MIR162x MON89034 (event code: SYN-BTØ11-1 x SYN-IR162-4 x MON-89Ø34-3, gene:pat) and Bt11 x MIR162 x MON89Ø34 x GA21 (event code: SYN-BTØ11-1 xSYN-IR162-4 x MON-89Ø34-3 x MON-ØØØ21-9, gene: pat), 59122 x DAS40278(event code: DAS-59122-7 x DAS-4Ø278-9, gene: pat), 59122 x MON810 xMIR604 (event code: DAS-59122-7 x MON-ØØ81Ø-6 x SYN-IR6Ø4-5, gene: pat),59122 x MON810 x NK603 x MIR604 (event code: DAS-59122-7 x MON-ØØ81Ø-6 xMON-ØØ6Ø3-6 x SYN-IR6Ø4-5, gene: pat), 59122 x MON88017 x DAS40278(event code: DAS-59122-7 x MON-88Ø17-3 x DAS-4Ø278-9, gene: pat), 59122x NK603 x MIR604 (event code: DAS-59122-7 x MON-ØØ6Ø3-6 x SYN-IR6Ø4-5,gene: pat), Bt11 x 5307 (event code: SYN-BTØ11-1 x SYN-Ø53Ø7-1, gene:pat), Bt11 x 5307 x GA21 (event code: SYN-BTØ11-1 x SYN-Ø53Ø7-1 xMON-ØØØ21-9, gene: pat), Bt11 x MIR162 x 5307 (event code: SYN-BTØ11-1 xSYN-IR162-4 x SYN-Ø53Ø7-1, gene: pat), Bt11 x MIR162 x 5307 x GA21(event code: SYN-BTØ11-1 x SYN-IR162-4 x SYN-Ø53Ø7-1 x MON-ØØØ21-9,gene: pat), BT11 x MIR162 x MIR604 x 5307 (event code: SYN-BTØ11-1 xSYN-IR162-4 x SYN-IR6Ø4-5 x SYN-Ø53Ø7-1, gene: pat), Bt11 x MIR162 xMIR604 x 5307 x GA21 (event code: SYN-BTØ11-1 x SYN-IR162-4 xSYN-IR6Ø4-5 x SYN-Ø53Ø7-1 x MON-ØØØ21-9, gene: pat), Bt11 x MIR162 xMIR604 x MON89034 x 5307 x GA21 (event code: SYN-BTØ11-1 x SYN-IR162-4 xSYN-IR6Ø4-5 x MON-89Ø34-3 x SYN-Ø53Ø7-1 x MON-ØØØ21-9, gene: pat), BT11x MIR162 x MIR604 x TC1507 (event code: SYN-BTØ11-1 x SYN-IR162-4 xSYN-IR6Ø4-5 x DAS-Ø15Ø7-1, gene: pat), BT11 x MIR162 x MIR604 x TC1507 x5307 (event code: SYN-BTØ11-1 x SYN-IR162-4 x SYN-IR6Ø4-5 x DAS-Ø15Ø7-1x SYN-Ø53Ø7-1, gene: pat), Bt11 x MIR162 x MIR604 x TC1507 x GA21 (eventcode: SYN-BTØ11-1 x SYN-IR162-4 x SYN-IR6Ø4-5 x DAS-Ø15Ø7-1 xMON-ØØØ21-9, gene: pat), Bt11 x MIR162 x TC1507 x 5307 (event code:SYN-BTØ11-1 x SYN-IR162-4 x DAS-Ø15Ø7-1 x SYN-Ø53Ø7-1, gene: pat), BT11x MIR162 x MIR604 x TC1507 x 5307 (event code: SYN-BTØ11-1 x SYN-IR162-4x SYN-IR6Ø4-5 x DAS-Ø15Ø7-1 x SYN-Ø53Ø7-1, gene: pat), Bt11 x MIR162 xMIR604 x TC1507 x GA21 (event code: SYN-BTØ11-1 x SYN-IR162-4 xSYN-IR6Ø4-5 x DAS-Ø15Ø7-1 x MON-ØØØ21-9, gene: pat), Bt11 x MIR162 xTC1507 x 5307 (event code: SYN-BTØ11-1 x SYN-IR162-4 x DAS-Ø15Ø7-1 xSYN-Ø53Ø7-1, gene: pat), Bt11 x MIR162 x TC1507 x 5307 x GA21 (eventcode: SYN-BTØ11-1 x SYN-IR162-4 x DAS-Ø15Ø7-1 x SYN-Ø53Ø7-1 xMON-ØØØ21-9, gene: pat), Bt11 x MIR604 x 5307 (event code: SYN-BTØ11-1 xSYN-IR6Ø4-5 x SYN-Ø53Ø7-1, gene: pat), Bt11 x MIR604 x 5307 x GA21(event code: SYN-BTØ11-1 x SYN-IR6Ø4-5 x SYN-Ø53Ø7-1 x MON-ØØØ21-9,gene: pat), Bt11 x MIR604 x TC1507 x 5307 (event code: SYN-BTØ11-1 xSYN-IR6Ø4-5 x DAS-Ø15Ø7-1 x SYN-Ø53Ø7-1, gene: pat), Bt11 x MIR604 xTC1507 x GA21 (event code: SYN-BTØ11-1 x SYN-IR6Ø4-5 x DAS-Ø15Ø7-1 xMON-ØØØ21-9, gene: pat), Bt11 x MON89034 (or Bt11 x MON89Ø34) (eventcode: SYN-BTØ11-1 x MON-89Ø34-3, gene: pat), Bt11 x MON89034 x GA21(event code: SYN-BTØ11-1 x MON-89Ø34-3 x MON-ØØØ21-9, gene: pat), Bt11 xMON89Ø34 x GA21 (event code: SYN-BTØ11-1 x MON-89Ø34-3 x MON-ØØØ21-9,gene: pat), Bt11 x TC1507 x 5307 (event code: SYN-BTØ11-1 x DAS-Ø15Ø7-1x SYN-Ø53Ø7-1, gene: pat), Bt11 x TC1507 x 5307 x GA21 (event code:SYN-BTØ11-1 x DAS-Ø15Ø7-1 x SYN-Ø53Ø7-1 x MON-ØØØ21-9, gene: pat),MIR162 x MIR604 x TC1507 x 5307 (event code: SYN-IR162-4 x SYN-IR6Ø4-5 xDAS-Ø15Ø7-1 x SYN-Ø53Ø7-1, gene: pat), MIR162 x MIR604 x TC1507 x 5307 xGA21 (event code: SYN-IR162-4 x SYN-IR6Ø4-5 x DAS-01507-1 x SYN-Ø53Ø7-1x MON-ØØØ21-9, gene: pat), MIR162 x MIR604 x TC1507 x GA21 (event code:SYN-IR162-4 x SYN-IR6Ø4-5 x DAS-Ø15Ø7-1 x MON-ØØØ21-9, gene: pat),MIR162 x TC1507 x 5307 (event code: SYN-IR162-4 x DAS-Ø15Ø7-1 xSYN-Ø53Ø7-1, gene: pat), MIR162 x TC1507 x 5307 x GA21 (event code:SYN-IR162-4 x DAS-Ø15Ø7-1 x SYN-Ø53Ø7-1 x MON-ØØØ21-9, gene: pat),MIR604 x TC1507 x 5307 (event code: SYN-IR6Ø4-5 x DAS-Ø15Ø7-1 xSYN-Ø53Ø7-1, gene: pat), MIR162 x TC1507 x 5307 (event code: SYN-IR162-4x DAS-Ø15Ø7-1 x SYN-Ø53Ø7-1, gene: pat), MIR162 x TC1507 x 5307 x GA21(event code: SYN-IR162-4 x DAS-Ø15Ø7-1 x SYN-Ø53Ø7-1 x MON-ØØØ21-9,gene: pat), MIR604 x TC1507 x 5307 (event code: SYN-IR6Ø4-5 xDAS-Ø15Ø7-1 x SYN-Ø53Ø7-1, gene: pat), MIR604 x TC1507 x 5307 x GA21(event code: SYN-IR6Ø4-5 x TC1507 x SYN-Ø53Ø7-1 x MON-ØØØ21-9, gene:pat), MIR604 x TC1507 x GA21 (event code: SYN-IR6Ø4-5 x TC1507 xMON-ØØØ21-9, gene: pat), MON87427 x 59122 (event code MON-87427-7 xDAS-59122-7: gene: pat), MON87427 x MON89034 x 59122 (event code:MON-87427-7 x MON-89Ø34-3 x DAS-59122-7, gene: pat), MON87427 x MON89034x MON88017 x 59122 (event code: MON-87427-7 x MON-89Ø34-3 x MON-88Ø17-3x 59122, gene: pat), MON87427 x MON89034 x TC1507 (event code:MON-87427-7 x MON-89Ø34-3 x DAS-Ø15Ø7-1, gene: pat), MON87427 x MON89034x TC1507 x 59122 (event code: MON-87427-7 x MON-89Ø34-3 x DAS-Ø15Ø7-1 xDAS-59122-7, gene: pat), MON87427 x MON89034 x TC1507 x MON87411 x 59122(event code: MON-87427-7 x MON-89Ø34-3 x DAS-Ø15Ø7-1 x MON-87411-9 xDAS-59122-7, gene: pat), MON87427 x MON89034 x TC1507 x MON87411 x 59122x DAS40278 (event code: MON-87427-7 x MON-89Ø34-3 x DAS-Ø15Ø7-1 xMON-87411-9 x DAS-59122-7 x DAS-4Ø278-9, gene: pat), MON87427 x MON89034x TC1507 x MON88017 (event code: MON-87427-7 x MON-89Ø34-3 x DAS-Ø15Ø7-1x MON-88Ø17-3, gene: pat), MON87427 x TC1507 (event code: MON-87427-7 xDAS-Ø15Ø7-1, gene: pat), MON87427 x TC1507 x 59122 (event code:MON-87427-7 x DAS-Ø15Ø7-1 x DAS-59122-7, gene: pat), MON87427 x TC1507 xMON88017 (event code: MON-87427-7 x DAS-Ø15Ø7-1 x MON-88Ø17-3, gene:pat), MON87427 x TC1507 x MON88017 x 59122 (event code: MON-87427-7 xDAS-Ø15Ø7-1 x MON-88Ø17-3 x DAS-59122-7, gene: pat), MON89034 x 59122 xDAS40278 (event code: MON-89Ø34-3 x DAS-59122-7 x DAS-40278-9, gene:pat), MON89034 x 59122 x MON88017 x DAS40278 (event code: MON-89Ø34-3 xDAS-59122-7 x MON-88Ø17-3 x DAS-4Ø278-9, gene: pat), MON89034 x TC1507 x59122 x DAS40278 (event code: MON-89Ø34-3 x DAS-Ø15Ø7-1 x DAS-59122-7 xDAS-4Ø278-9, gene: pat), MON89Ø34 x TC1507 x DAS40278 (event code:MON-89Ø34-3 x DAS-Ø15Ø7-1 x DAS-4Ø278-9, gene: pat), MON89034 x TC1507 xNK603 x MIR162 (event code: MON-89Ø34-3 x DAS-Ø15Ø7-1 x MON-ØØ6Ø3-6 xSYN-IR162-4, gene: pat), TC1507 x 5307 (event code: DAS-Ø15Ø7-1 xSYN-Ø53Ø7-1, gene: pat), TC1507 x 5307 x GA21 (event code: DAS-Ø15Ø7-1 xSYN-Ø53Ø7-1 x MON-ØØØ21-9, gene: pat), TC1507 x 59122 x DAS40278 (eventcode: DAS-Ø15Ø7-1 x DAS-59122-7 x DAS-4Ø278-9, gene: pat), TC1507 x59122 x MON810 x MIR604 (event code: DAS-Ø15Ø7-1 x DAS-59122-7 xMON-ØØ81Ø-6 x SYN-IR6Ø4-5, gene: pat), TC1507 x 59122 x MON88017 xDAS40278 (event code: DAS-Ø15Ø7-1 x DAS-59122-7 x MON-88Ø17-3 xDAS-4Ø278-9, gene: pat), TC1507 x 59122 x NK603 x MIR604 (event code:gene: pat) DAS-Ø15Ø7-1 x DAS-59122-7 x MON-ØØ6Ø3-6 x SYN-IR6Ø4-5, TC1507x DAS40278 (event code: DAS-Ø15Ø7-1 x DAS-4Ø278-9, gene: pat), TC1507 xMON810 x MIR604 (event code: DAS-Ø15Ø7-1 x MON-ØØ81Ø-6 x SYN-IR6Ø4-5,gene: pat), TC1507 x MON810 x NK603 x MIR604 (event code: DAS-Ø15Ø7-1 xMON-ØØ81Ø-6 x MON-ØØ6Ø3-6 x SYN-IR6Ø4-5, gene: pat), TC1507 x MON88017 xDAS40278 (event code: DAS-Ø15Ø7-1 x MON-88Ø17-3 x DAS-4Ø278-9, gene:pat) and TC1507 x NK603 x DAS40278 (event code: DAS-Ø15Ø7-1 xMON-ØØ6Ø3-6 x DAS-4Ø278-9, gene: pat).

Transgenic soybean events comprising glufosinate tolerance genes are forexample, but not excluding others, A2704-12 (event code: ACS-GMØØ5-3,gene: pat, e.g. commercially available as Liberty Link™ soybean),A2704-21 (event code: ACS-GMØØ4-2, gene: pat, e.g. commerciallyavailable as Liberty Link™ soybean), A5547-127 (event code: ACS-GMØØ6-4,gene: pat, e.g. commercially available as Liberty Link™ soybean),A5547-35 (event code: ACS-GMØØ8-6, gene: pat, e.g. commerciallyavailable as Liberty Link™ soybean), GU262 (event code: ACS-GMØØ3-1,gene: pat, e.g. commercially available as Liberty Link™ soybean), W62(event code: ACS-GMØØ2-9, gene: pat, e.g. commercially available asLiberty Link™ soybean), W98 (event code: ACS-GMØØ1-8, gene: pat, e.g.commercially available as Liberty Link™ soybean), DAS68416-4 (eventcode: DAS-68416-4, gene: pat, e.g. commercially available as Enlist™Soybean), DAS44406-6 (event code: DAS-44406-6, gene: pat), DAS68416-4 xMON89788 (event code: DAS-68416-4 x MON-89788-1, gene: pat), SYHTOH2(event code: SYN-ØØØH2-5, gene: pat), DAS81419 x DAS444Ø6-6 (event code:DAS-81419-2 x DAS-444Ø6-6, gene: pat) and FG72 x A5547-127 (event code:MST-FGØ72-3 x ACS-GMØØ6-4, gene: pat).

Transgenic cotton events comprising glufosinate tolerance genes are forexample, but not excluding others, 3006-210-23 x 281-24-236 x MON1445(event code: DAS-21Ø23-5 x DAS-24236-5 x MON-Ø1445-2, gene: bar, e.g.commercially available as WideStrike™ Roundup Ready™ Cotton),3006-210-23 x 281-24-236 x MON88913 (event code: DAS-21Ø23-5 xDAS-24236-5 x MON-88913-8, gene: bar, e.g. commercially available asWidestrike™ Roundup Ready Flex™ Cotton), 3006-210-23 x 281-24-236 xMON88913 x COT102 (event code: DAS-21Ø23-5 x DAS-24236-5 x MON-88913-8 xSYN-IR102-7, gene: pat, e.g. commercially available as Widestrike™ xRoundup Ready Flex™ x VIPCOT™ Cotton), GHB614 x LLCotton25 (event code:BCS-GHØØ2-5 x ACS-GHØØ1-3, gene: bar, e.g. commercially available asGlyTol™ Liberty Link™), GHB614 x T304-40 x GHB119 (event code:BCS-GHØØ2-5 x BCS-GHØØ4-7 x BCS-GHØØ5-8, gene: bar, e.g. commerciallyavailable as Glytol™ x Twinlink™) LLCotton25 (event code: ACS-GHØØ1-3,gene: bar, e.g. commercially available as ACS-GHØØ1-3), GHB614 x T304-40x GHB119 x COT102 (event code: BCS-GHØØ2-5 x BCS-GHØØ4-7 x BCS-GHØØ5-8 xSYN-IR102-7, gene: bar, e.g. commercially available as Glytol™ xTwinlink™ x VIPCOT™ Cotton), LLCotton25 x MON15985 (event code:ACS-GHØØ1-3 x MON-15985-7, gene: bar, e.g. commercially available asFibermax™ Liberty Link™ Bollgard II™), T304-40 x GHB119 (event code:BCS-GHØØ4-7 x BCS-GHØØ5-8, gene: bar, e.g. commercially available asTwinLink™ Cotton), GHB614 x T304-40 x GHB119 x COT102 (event code:BCS-GHØØ2-5 x BCS-GHØØ4-7 x BCS-GHØØ5-8 x SYN-IR1Ø2-7, gene: bar, e.g.commercially available as Glytol™ x Twinlink™ x VIPCOT™ Cotton), GHB119(event code: BCS-GHØØ5-8, gene: bar), GHB614 x LLCotton25 x MON15985(event code: CS-GHØØ2-5 x ACS-GHØØ1-3 x MON-15985-7, gene: bar), MON887Ø1-3 (event code: MON88701, gene: bar), T303-3 (event code:BCS-GHØØ3-6, gene: bar), T304-40 (event code: BCS-GHØØ3-6, gene: bar),(event code: BCS-GHØØ4-7, gene: bar), 81910 (event code: DAS-81910-7,gene: pat), MON8870 (event code: MON 887Ø1-3, gene: bar), MON88701 xMON88913 (event code: MON 887Ø1-3 x MON-88913-8, gene: bar), MON88701 xMON88913 x MON15985 (event code: MON 887Ø1-3 x MON-88913-8 xMON-15985-7, gene: bar), 281-24-236 x 33 3006-210-23 x COT102 x 81910(event code: DAS-24236-5 x DAS-21Ø23-5 x SYN-IR1Ø2-7 x DAS-81910-7,gene: pat), COT102 x MON15985 x MON88913 x MON88701 (event code:SYN-IR1Ø2-7 x MON-15985-7 x MON-88913-8 x MON 887Ø1-3, gene: bar) and3006-210-23 x 281-24-236 x MON88913 x COT102 x 81910 (event code:DAS-21Ø23-5 x DAS-24236-5 x MON-88913-8 x SYN-IR1Ø2-7 x DAS-81910-7,gene: pat).

Transgenic canola events comprising glufosinate tolerance genes are forexample, but not excluding others, HCN10 (Topas 19/2) (event code: gene:bar, e.g. commercially available as Liberty Link™ Independence™), HCN28(T45) (event code: ACS-BNØØ8-2, gene: pat, e.g. commercially availableas InVigor™ Canola), HCN92 (Topas 19/2 (event code: ACS-BNØØ7-1, gene:bar, e.g. commercially available as Liberty Link™ Innovator™), MS1(B91-4) (event code: ACS-BNØØ4-7, gene: bar, e.g. commercially availableas InVigor™ Canola), MS1 x RF1 (PGS1) (event code: ACS-BNØØ4-7 xACS-BNØØ1-4, gene: bar, e.g. commercially available as InVigor™ Canola),MS1 x RF2 (PGS2) (event code: ACS-BNØØ4-7 x ACS-BNØØ2-5, gene: bar, e.g.commercially available as InVigor™ Canola), MS1 x RF3 (event code:ACS-BNØØ4-7 x ACS-BNØØ3-6, gene: bar, e.g. commercially available asInVigor™ Canola), MS8 (event code: ACS-BNØØ5-8, gene: bar, e.g.commercially available as InVigor™ Canola), MS8 x RF3 (event code:ACS-BNØØ5-8 x ACS-BNØØ3-6, gene: bar, e.g. commercially available asInVigor™ Canola), RF1 (B93-101) (event code: ACS-BNØØ1-4, gene: bar,e.g. commercially available as InVigor™ Canola), RF2 (B94-2) (eventcode: ACS-BNØØ2-5, gene: bar, e.g. commercially available as InVigor™Canola), RF3 (event code: ACS-BNØØ3-6, gene: bar, e.g. commerciallyavailable as InVigor™ Canola), MS1 x MON88302 (event code: ACS-BNØØ4-7 xMON-883Ø2-9, gene: bar, e.g. commercially available as InVigor™ xTruFlex™ Roundup Ready™ Canola), MS8 x MON88302 (event code: ACS-BNØØ5-8x MON-883Ø2-9, gene: bar, e.g. commercially available as InVigor™ xTruFlex™ Roundup Ready™ Canola), RF1 x MON88302 (event code: ACS-BNØØ1-4x MON-883Ø2-9, gene: bar, e.g. commercially available as InVigor™ xTruFlex™ Roundup Ready™ Canola), RF2 x MON88302 (event code: ACS-BNØØ2-5x MON-883Ø2-9, gene: bar, e.g. commercially available as InVigor™ xTruFlex™ Roundup Ready™ Canola), HCN28 x MON88302 (event code:ACS-BNØØ8-2 x MON-883Ø2-9, gene: pat, e.g. commercially available asInVigor™ x TruFlex™ Roundup Ready™ Canola), HCN92 x MON88302 (eventcode: ACS-BNØØ7-1 x MON-883Ø2-9, gene: bar, e.g. commercially availableas Liberty Link™ Innovator™ x TruFlex™ Roundup Ready™ Canola), HCR-1(gene: pat), MON88302 x MS8 x RF3 (event code: MON-883Ø2-9 x ACS-BNØØ5-8x ACS-BNØØ3-6, gene: bar), MON88302 x RF3 (event code: MON-883Ø2-9 xACS-BNØØ3-6, gene: bar), MS8 x RF3 x GT73 (RT73) (event code: gene:bar), PHY14 (event code: ACS-BNØØ5-8 x ACS-BNØØ3-6 x MON-ØØØ73-7, gene:bar), PHY23 (gene: bar), PHY35 (gene: bar) and PHY36 (gene: bar) and73496 x RF3 (event code: DP-Ø73496-4 x ACS-BNØØ3-6, gene: bar).

Transgenic rice events comprising glufosinate tolerance genes are forexample, but not excluding others, LLRICE06 (event code: ACS-OSØØ1-4,e.g. commercially available as Liberty Link™ rice), LLRICE601 (eventcode: BCS-OSØØ3-7, e.g. commercially available as Liberty Link™ rice)and LLRICE62 (event code: ACS-OSØØ2-5, e.g. commercially available asLiberty Link™ rice).

The herbicidal compositions have an outstanding herbicidal activityagainst a broad spectrum of economically important harmfulmonocotyledonous and dicotyledonous harmful plants. Also here,post-emergence application is preferred.

Specifically, examples may be mentioned of some representatives of themonocotyledonous and dicotyledonous weed flora which can be controlledby the combinations according to the invention, without the enumerationbeing a restriction to certain species.

In the context of the present text, reference may be made to growthstages according to the BBCH monograph “Growth stages of mono- anddicotyledonous plants”, 2nd edition, 2001, ed.

Uwe Meier, Federal Biological Research Centre for Agriculture andForestry (Biologische Bundesanstalt für Land und Forstwirtschaft).

Examples of monocotyledonous harmful plants on which the glufosinatecombinations act efficiently are from amongst the genera Hordeum spp.,Echinochloa spp., Poa spp., Bromus spp., Digitaria spp., Eriochloa spp.,Setaria spp., Pennisetum spp., Eleusine spp., Eragrostis spp., Panicumspp., Lolium spp., Brachiaria spp., Leptochloa spp., Avena spp., Cyperusspp., Axonopris spp., Sorghum spp., and Melinus spp.

Particular examples of monocotyledonous harmful plants species on whichthe herbicidal compositions act efficiently are selected from amongstthe species Hordeum murinum, Echinochloa crus-galli, Poa annua, Bromusrubens L., Bromus rigidus, Bromus secalinus L., Digitaria sanguinalis,Digitaria insularis, Eriochloa gracilis, Setaria faberi, Setariaviridis, Pennisetum glaucum, Eleusine indica, Eragrostis pectinacea,Panicum miliaceum, Lolium multiflorum, Brachiaria platyphylla,Leptochloa fusca, Avena fatua, Cyperus compressus, Cyperus esculentes,Axonopris offinis, Sorghum halapense, and Melinus repens.

In a preferred embodiment, the herbicidal compositions are used tocontrol monocotyledonous harmful plant species, more preferablymonocoty-ledonous plants of the species Echinochloa spp., Digitariaspp., Setaria spp., Eleusine spp. and Bra-chiarium spp.

Examples of dicotyledonous harmful plants on which the herbicidalcompositions act efficiently are from amongst the genera Amaranthusspp., Erigeron spp., Conyza spp., Polygonum spp., Medicago spp., Mollugospp., Cyclospermum spp., Stellaria spp., Gnaphalium spp., Taraxacumspp., Oenothera spp., Amsinckia spp., Erodium spp., Erigeron spp.,Senecio spp., Lamium spp., Kochia spp., Chenopodium spp., Lactuca spp.,Malva spp., Ipomoea spp., Brassica spp., Sinapis spp., Urtica spp., Sidaspp, Portulaca spp., Richardia spp., Ambrosia spp., Calandrinia spp.,Sisymbrium spp., Sesbania spp., Capsella spp., Sonchus spp., Euphorbiaspp., Helianthus spp., Coronopus spp., Salsola spp., Abutilon spp.,Vicia spp., Epilobium spp., Cardamine spp., Picris spp., Trifolium spp.,Galinsoga spp., Epimedium spp., Marchantia spp., Solanum spp., Oxalisspp., Metricaria spp., Plantago spp., Tribulus spp., Cenchrus spp.Bidens spp., Veronica spp., and Hypochaeris spp.

Particular examples of dicotyledonous harmful plants species on whichthe herbicidal compositions act efficiently are selected from amongstthe species Amaranthus spinosus, Polygonum convolvulus, Medicagopolymorpha, Mollugo verticillata, Cyclospermum leptophyllum, Stellariamedia, Gnaphalium purpureum, Taraxacum offi cinale, Oenothera laciniata,Amsinckia intermedia, Erodium cicutarium, Erodium moschatum, Erigeronbonariensis (Conyza bonariensis), Senecio vulgaris, Lamium amplexicaule,Erigeron canadensis, Polygonum aviculare, Kochia scoparia, Chenopodiumalbum, Lactuca serriola, Malva parviflora, Malva neglecta, Ipomoeahederacea, Ipomoea lacunose, Brassica nigra, Sinapis arvensis, Urticadioica, Amaranthus blitoides, Amaranthus retroflexus, Amaranthushybridus, Amaranthus lividus, Sida spinosa, Portulaca oleracea,Richardia scabra, Ambrosia artemisiifolia, Calandrinia cau-lescens,Sisymbrium irio, Sesbania exaltata, Capsella bursa-pastoris, Sonchusoleraceus, Euphorbia maculate, Helianthus annuus, Coronopus didymus,Salsola tragus, Abutilon theophrasti, Vicia ben-ghalensis L., Epilobiumpaniculatum, Cardamine spp, Picris echioides, Trifolium spp., Galinsogaspp., Epimedium spp., Marchantia spp., Solanum spp., Oxalis spp.,Metricaria matriccarioides, Plantago spp., Tribulus terrestris, Salsolakali, Cenchrus spp., Bidens bipinnata, Veronica spp., and Hypochaerisradicata.

In a preferred embodiment, the herbicidal compositions are used tocontrol dicotyledonous harmful plant species, more preferablydicotyledonous plants of the species Amaranthus spp., Erigeron spp.,Conyza spp., Kochia spp. and Abutilon spp.

Herbicidal compositions are also suitable for controlling a large numberof annual and perennial sedge weeds including Cyperus species such aspurple nutsedge (Cyperus rotundus L.), yellow nutsedge (Cyperusesculentus L.), hime-kugu (Cyperus brevifolius H.), sedge weed (Cyperusmicroiria Steud), rice flatsedge (Cyperus iria L.), Cyperus difformis,Cyperus difformis L., Cyperus esculentus, Cyperus ferax, Cyperus flavus,Cyperus iria, Cyperus lanceolatus, Cyperus odoratus, Cyperus rotundus,Cyperus serotinus Rottb., Eleocharis acicularis, Eleocharis kuroguwai,Fimbristylis dichotoma, Fimbristylis miliacea, Scirpus grossus, Scirpusjuncoides, Scirpus juncoides Roxb, Scirpus or Bolboschoenus maritimus,Scirpus or Schoenoplectus mucronatus, Scirpus planiculmis Fr. schmidtand the like.

If the herbicidal compositions are applied post-emergence to the greenparts of the plants, growth likewise stops drastically a very short timeafter the treatment and the weed plants remain at the growth stage ofthe point of time of application, or they die completely after a certaintime, so that in this manner competition by the weeds, which is harmfulto the crops, is eliminated at a very early point in time and in asustained manner.

The herbicidal compositions are characterized by a rapidly commencingand long-lasting herbicidal action. As a rule, the rainfastness of theactive compounds in the herbicide combinations according to the presentinvention is advantageous. In particular when the herbicidalcompositions are employed application rates may be reduced, a broaderspectrum of broad-leaved weeds and grass weeds maybe controlled, theherbicidal action may take place more rapidly, the duration of actionmay be longer, the harmful plants may be controlled better while usingonly one, or few, applications, and the application period which ispossible to be extended.

The abovementioned properties and advantages are of benefit for weedcontrol practice to keep agricultural crops free from undesiredcompeting plants and thus to safeguard and/or increase the yields fromthe qualitative and/or quantitative point of view. These herbicidalcompositions markedly exceed the technical state of the art with a viewto the properties described. Owing to their herbicidal andplant-growth-regulatory properties, the herbicidal compositions can beemployed for controlling harmful plants in genetically modified crops orcrops obtained by mutation/selection. These crops are distinguished as arule by particular, advantageous properties, such as resistances toherbicidal compositions or resistances to plant diseases or causativeagents of plant diseases such as particular insects or microorganismssuch as fungi, bacteria or viruses. Other particular properties relate,for example, to the harvested material with regard to quantity, quality,storability, composition and specific constituents. Thus, for example,transgenic plants are known whose starch content is increased or whosestarch quality is altered, or those where the harvested material has adifferent fatty acid composition.

The present invention also relates to a method of controlling undesiredvegetation (e.g. harmful plants), which comprises applying theherbicidal compositions, preferably by the post-emergence method, toharmful or undesired plants, parts of said harmful or undesired plants,or the area where the harmful or undesired plants grow, for example thearea under cultivation.

In the context of the present invention “controlling” denotes asignificant reduction of the growth of the harmful plant(s) incomparison to the untreated harmful plants. Preferably, the growth ofthe harmful plant(s) is essentially diminished (60-79%), more preferablythe growth of the harmful plant(s) is largely or fully suppressed(80-100%), and in particular the growth of the harmful plant(s) isalmost fully or fully suppressed (90-100%).

Thus, in a further aspect, the present invention relates to a method forcontrolling undesired plant growth, and/or controlling harmful plants,comprising the step of applying the herbicidal composition (preferablyin one of the preferred embodiments defined herein) onto the undesiredplants or the harmful plants, on parts of the undesired plants or theharmful plants, or on the area where the undesired plants or the harmfulplants grow.

The herbicidal composition(s) may be used for controlling undesirablevegetation in burndown programs, in industrial vegetation management andforestry, in vegetable and perennial crops and in turf and lawn, whereinthe herbicidal composition(s) can be applied pre- or post-emergence,i.e. before, during and/or after emergence of the undesirable plants.Preferred is the application as post-emergence treatment, i.e. duringand/or after emergence of the undesirable plants. Herein, the herbicidalcomposition(s) are applied to a locus where crops will be planted beforeplanting or emergence of the crop.

In industrial weed management and forestry, it is desirable to control abroad range of weeds for an extended period of time. The control oflarge weeds, or taller species such as bushes or trees may also bedesirable. Industrial weed management includes for example railway andright-of-way management, fence lines and non-crop land such asindustrial and building sites, gravel areas, roads or sidewalks.Forestry includes for example the clearing of existing forest orbushland, the removal of regrowth after mechanical forest cutting, orthe management of weeds under forestry plantations. In the latter case,it may be desirable to shield desirable trees from contact with thespray solution that contains the herbicidal mixture according to thepresent invention.

The herbicidal composition can also be used for weed control in turf andlawn provided the desirable grass species are tolerant to herbicidalcomposition. In particular, such herbicidal compositions can be used indesirable grass that has been rendered tolerant to the respectiveagrochemical active ingredient, e.g. glufosinate or its salts, bymutagenesis or genetic engineering.

Glufosinate and its salts are non-selective systemic herbicides having agood post-emergence activity against numerous weeds and thus can be usedin burndown programs, in industrial vegetation management and forestry,in vegetable and perennial crops and in turf and lawn.

Therefore, the present invention also relates to a method for burndowntreatment of undesirable vegetation in crops, comprising applying theherbicidal composition, to a locus where crops will be planted beforeplanting (or seeding) or emergence of the crop. Herein, the herbicidalcomposition is applied undesirable vegetation or the locus thereof.

The present invention also relates to a method for controllingundesirable vegetation, which method comprises applying the herbicidalcomposition, to a locus where undesirable vegetation is present or isexpected to be present. The application may be done before, duringand/or after, preferably during and/or after, the emergence of theundesirable vegetation. In one embodiment, the application is carriedout before emergence of the crop, which is cultivated at the locus wherethe undesirable vegetation is present or is expected to be present. Inanother embodiment, the application is carried out before planting thecrop.

As used herein, the terms “controlling” and “combating” are synonyms.

As used herein, the terms “undesirable vegetation”, “undesirablespecies”, “undesirable plants”, “harmful plants”, “undesirable weeds”,or “harmful weeds” are synonyms.

The term “locus”, as used herein, means the area in which the vegetationor plants are growing or will grow, typically a field.

In burndown programs, the herbicidal composition(s) can be applied priorto seeding (planting) or after seeding (or planting) of the crop plantsbut before the emergence of the crop plants, in particular prior toseeding. The herbicidal compositions are preferably applied prior toseeding of the crop plants. For burndown, the herbicidal composition(s)will generally be applied a date up to 9 months, frequently up to 6months, preferably up to 4 months prior to planting the crop. Theburndown application can be done at a date up to 1 day prior toemergence of the crop plant and is preferably done at a date prior toseeding/planting of the crop plant, preferably at a date of at least oneday, preferably at least 2 days and in particular at least one 4 daysprior to planting or from 6 months to 1 day prior emergence, inparticular from 4 months to 2 days prior emergence and more preferablyfrom 4 months to 4 days prior emergence. It is, of course, possible torepeat the burndown application once or more, e.g. once, twice, threetimes, four times or five times within that time frame.

It is a particular benefit of the herbicidal compositions that they havea very good post-emergence herbicide activity, i.e. they show a goodherbicidal activity against emerged undesirable plants. Thus, in apreferred embodiment of invention, the herbicidal compositions areapplied post-emergence, i.e. during and/or after, the emergence of theundesirable plants. It is particularly advantageous to apply theherbicidal composition post emergent when the undesirable plant startswith leaf development up to flowering. The herbicidal compositions areparticularly useful for controlling undesirable vegetation which hasalready developed to a state, which is difficult to control withconventional burndown mixtures, i.e. when the individual weed is tallerthan 10 cm (4 inches) or even taller than 15 cm (6 inches) and/or forheavy weed populations.

In the case of a post-emergence treatment of the plants, the herbicidalcompositions are preferably applied by foliar application.

The herbicidal compositions can be applied in conventional manner byusing techniques as skilled person is familiar with. Suitable techniquesinclude spraying, atomizing, dusting, spreading or watering. The type ofapplication depends on the intended purpose in a well-known manner; inany case, they should ensure the finest possible distribution of theactive ingredients according to the invention.

In one embodiment, the herbicidal compositions are applied to locusmainly by spraying, in particular foliar spraying of an aqueous dilutionof the active ingredients of the mixture. Application can be carried outby customary spraying techniques using, for example, water as carrierand spray liquor rates of from about 10 to 2000 I/ha or 50 to 1000 I/ha(for example from 100 to 500 I/ha). Application of the inventivemixtures by the low-volume and the ultra-low-volume method is possible,as is their application in the form of microgranules.

The required application rate of the herbicidal composition depends onthe density of the undesired vegetation, on the development stage of theplants, on the climatic conditions of the location where the mixture isused and on the application method.

In general, the rate of application of L-glufosinate or its salt isusually from 50 g/ha to 3000 g/ha and preferably in the range from 100g/ha to 2000 g/ha or from 200 g/ha to 1500 g/ha of active substance(a.i.).

When using the herbicidal composition in the methods of the presentinvention, the glufosinate or a salt thereof and the compound of formula(I) can be applied simultaneously or in succession, where undesirablevegetation may occur. Herein, it is immaterial whether the individualcompounds present in the inventive mixtures are formulated jointly orseparately and applied jointly or separately, and, in the case ofseparate application, in which order the application takes place. It isonly necessary, that the individual compounds present in the inventivemixtures are applied in a time frame, which allows simultaneous actionof the active ingredients and/or the compound of formula (I) on theundesirable plants.

The herbicidal compositions show a persistent herbicidal activity, evenunder difficult weathering conditions, which allows a more flexibleapplication in burndown applications and minimizes the risk of weedsescaping. Apart from that, the herbicidal compositions show superiorcrop compatibility with certain conventional crop plants and withherbicide tolerant crop plants, i.e. their use in these crops leads to areduced damage of the crop plants and/or does not result in increaseddamage of the crop plants. Thus, the herbicidal compositions can also beapplied after the emergence of the crop plants. The herbicidalcompositions may also show an accelerated action on harmful plants, i.e.they may affect damage of the harmful plants more quickly.

The herbicidal compositions are also suitable for controlling weeds thatare resistant to commonly used herbicides such as, for example, weedsthat are resistant to glyphosate, weeds that are resistant to auxininhibitor herbicides such as e. g. 2,4-D or dicamba, weeds that areresistant to photosynthesis inhibitors such as e. g. atrazine, weedsthat are resistant to ALS inhibitors such as e. g. sulfonylureas,imidazolinones or triazolopyrimidines, weeds that are resistant toACCase inhibitors such as e. g. clodinafop, clethodim or pinoxaden orweeds that are resistant to protoporphyrinogen-IX-oxidase inhibitorssuch as e. g. sulfentrazone, flumioxazine, fomesafen or acifluorfen, forexample the weeds that are listed in the International Survey ofResistant Weeds(http://www.weedscience.org/Summary/SpeciesbySOATable.aspx). Inparticular, they are suitable for controlling the resistant weeds thatare resistant go glufosinate or its salts, such as listed in theInternational Survey of Resistant Weeds, for example ACCase resistantEchinochloa crus-galli, Avena fatua, Alopecurus myosuroides, Echinochloacolona, Alopecurus japonicus, Bromus tectorum, Hordeum murinum,Ischaemum rugosum, Setaria viridis, Sorghum halepense, Alopecurusaequalis, Apera spica-venti, Avena sterilis, Beckmannia szygachne,Bromus diandrus, Digitaria sanguinalis, Echinocloa oryzoides,Echinochloa phyllopogon, Phalaris minor, Phalaris paradoxa, Setariafaberi, Setaria viridis, Brachypodium distachyon, Bromus diandrus,Bromus sterilis, Cynosurus echinatus, Digitaria insularis, Digitariaischaemum, Leptochloa chinensis, Phalaris brachystachis, Rotboelliacochinchinensis, Digitaria ciliaris, Ehrharta longiflora, Eriochloapunctata, Leptochloa panicoides, Lolium persicum, Polypogon fugax,Sclerochloa kengiana, Snowdenia polystacha, Sorghum sudanese andBrachiaria plantaginea, ALS inhibitor resistant Echinochloa crus-galli,Poa annua, Avena fatua, Alopecurus myosuroides, Echinochloa colona,Amaranthus hybridus, Amaranthus palmeri, Amaranthus rudis, Conyzasumatrensis, Amaranthus retroflexus, Ambrosia artemisifolia, Conyzacanadensis, Kochia scoparia, Raphanus raphanistrum, Senecio vernalis,Alopecurus japonicus, Bidens pilosa, Bromus tectorum, Chenopodium album,Conyza bonariensis, Hordeum murinum, Ischaemum rugosum, Seneciovulgaris, Setaria viridis, Sisymbrium orientale, Sorghum halepense,Alopecurus aequalis, Amaranthus blitum, Amaranthus powellii, Aperaspica-venti, Avena sterilis, Brassica rapa, Bromus diandrus, Descurainiasophia, Digitaria sanguinalis, Echinochloa oryzoides, Echinochloaphyllopogon, Euphorbia heterophylla, Lactuca serriola, Phalaris minor,Phalaris paradoxa, Setaria faberi, Setaria viridis, Sinapis arvensis,Solanum ptycanthum, Sonchus oleraceus, Stellaria media, Amaranthusblitoides, Amaranthus spinosus, Amaranthus viridis, Ambrosia trifida,Bidens subalternans, Bromus diandrus, Bromus sterilis, Capsellabursapastoris, Centaurea cyanus, Cynosurus echinatus, Cyperus difformis,Fimbristilis miliacea, Galeopsis tetrahit, Galium aparine, Galiumspurium, Helianthus annuus, Hirschfeldia incana, Limnocharis flava,Limnophila erecta, Papaver rhoeas, Parthenium hysterophorus, Phalarisbrachystachis, Polygonum convolvulus, Polygonum lapathifolium, Polygonumpersicaria, Ranunculus acris, Rottboellia cochinchinensis, Sagittariamontevidensis, Salsola tragus, Schoenoplectus mucronatus, Setariapumila, Sonchus asper, Xanthium strumarium, Ageratum conyzoides, Alismacanaliculatum, Alisma plantago-aquatica, Ammannia auriculata, Ammanniacoccinea, Ammannia arvensis, Anthemis cotula, Bacopa rotundifolia,Bifora radians, Blyxa aubertii, Brassica tournefortii, Bromus japonicus,Bromus secalinus, Lithospermum arvense, Camelina microcarpa, Chamaesycemaculata, Chrysanthemum coronarium, Clidemia hirta, Crepis tectorum,Cuscuta pentagona, Cyperus brevifolis, Cyperus compressus, Cyperusesculentus, Cyperus iria, Cyperus odoratus, Damasonium minus, Diplotaxiserucoides, Diplotaxis tenuifolia, Dopatrum junceum, Echium plantagineum,Elatine triandra, Eleocharis acicularis, Erucaria hispanica, Erysimumrepandum, Galium tricornutum, Iva xanthifolia, Ixophorus unisetus,Lamium amplexicaule, Limnophilia sessiliflora, Lindernia dubia,Lindernia micrantha, Lindernia procumbens, Ludwigia prostrata,Matricaria recutita, Mesembryanthemum crystallinum, Monochoriakorsakowii, Monochoria vaginalis, Myosoton aquaticum, Neslia paniculata,Oryza sativa var. sylvatica, Pentzia suffruticosa, Picris hieracioides,Raphanus sativus, Rapistrum rugosum, Rorippa indica, Rotala indica,Rotala pusilla, Rumex dentatus, Sagittaria guayensis, Sagittariapygmaea, Sagittaria trifolia, Schoenoplectus fluviatilis, Schoenoplectusjuncoides, Schoenoplectus wallichii, Sida spinosa, Silene gallica,Sinapis alba, Sisymbrium thellungii, Sorghum bicolor, Spergula arvensis,Thlaspi arvense, Tripleurospermum perforatum, Vaccaria hispanica andVicia sativa, photosynthesis inhibitor resistant Echinochloa crus-galli,Poa annua, Alopecurus myosuroides, Echinochloa colona, Amaranthushybridus, Amaranthus palmeri, Amaranthus rudis, Conyza sumatrensis,Amaranthus retroflexus, Ambrosia artemisifolia, Conyza canadensis,Kochia scoparia, Raphanus raphanistrum, Senecio vernalis, Alopecurusjaponicus, Bidens pilosa, Bromus tectorum, Chenopodium album, Conyzabonariensis, Ischaemum rugosum, Senecio vulgaris, Setaria viridis,Sisymbrium orientale, Amaranthus blitum, Amaranthus powellii, Aperaspica-venti, Beckmannia syzigachne, Brassica rapa, Digitariasanguinalis, Euphorbia heterophylla, Phalaris minor, Phalaris paradoxa,Setaria faberi, Setaria viridis, Sinapis arvensis, Solanum ptycanthum,Stellaria media, Amaranthus blitoides, Amaranthus viridis, Bidenssubalternans, Brachypodium distachyon, Capsella bursa-pastoris, Chlorisbarbata, Cyperus difformis, Echinochloa erecta, Epilobium ciliatum,Polygonum aviculare, Polygonum convolvulus, Polygonum lapathifolium,Polygonum persicaria, Portulaca oleracea, Schoenoplectus mucronatus,Setaria pumila, Solanum nigrum, Sonchus asper, Urochloa panicoides,Vulpia bromoides, Abutilon theophrasti, Amaranthus albus, Amaranthuscruentus, Arabidopsis thaliana, Arenaria serpyllifolia, Bidenstripartita, Chenopodium album, Chenopodium ficifolium, Chenopodiumpolyspermum, Crypsis schoenoides, Datura stramonium, Epilobiumtetragonum, Galinsoga ciliata, Matricaria discoidea, Panicum capillare,Panicum dichotomiflorum, Plantago lagopus, Polygonum hydopiper,Polygonum pensylvanicum, Polygonum monspeliensis, Rostraria, smyrnacea,Rumex acetosella, Setaria verticillata and Urtica urens, PS-I-electrondiversion inhibitor resistant Poa annua, Conyza sumatrensis, Conyzacanadensis, Alopecurus japonicus, Bidens pilosa, Conyza bonariensis,Hordeum murinum, Ischaemum rugosum, Amaranthus blitum, Solanumptycanthum, Arctotheca calendula, Epilobium ciliatum, Hedyotisverticillata, Solanum nigrum, Vulpia bromoides, Convolvulus arvensis,Crassocephalum crepidioides, Cuphea carthagensis, Erigeronphiladelphicus, Gamochaeta pensylvanica, Landoltia punctata, Lepidiumvirginicum, Mazus fauriei, Mazus pumilus, Mitracarpus hirtus,Sclerochloa dura, Solanum americanum and Youngia japonica, glyphosateresistant Poa annua, Echinochloa colona, Amaranthus hybridus, Amaranthuspalmeri, Amaranthus rudis, Conyza sumatrensis, Ambrosia artemisifolia,Conyza canadensis, Kochia scoparia, Raphanus raphanistrum, Bidenspilosa, Conyza bonariensis, Hordeum murinum, Sorghum halepense, Brassicarapa, Bromus diandrus, Lactuca serriola, Sonchus oleraceus, Amaranthusspinosus, Ambrosia trifida, Digitaria insularis, Hedyotis verticillata,Helianthus annuus, Parthenium hysterophorus, Plantago lanceolata,Salsola tragus, Urochloa panicoides, Brachiaria eruciformis, Bromusrubens, Chloris elata, Chloris truncata, Chloris virgata, Cynodonhirsutus, Lactuca saligna, Leptochloa virgata, Paspalum paniculatum andTridax procumbens, microtubule assembly inhibitor resistant Echinochloacrusgalli, Poa annua, Avena fatua, Alopecurus myosuroides, Amaranthuspalmeri, Setaria viridis, Sorghum halepense, Alopecurus aequalis,Beckmannia syzigachne and Fumaria densifloria, auxin herbicide resistantEchinochloa crus-galli, Echinochloa colona, Amaranthus hybridus,Amaranthus rudis, Conyza sumatrensis, Kochia scoparia, Raphanusraphanistrum, Chenopodim album, Sisymbrium orientale, Descurainiasophia, Lactuca serriola, Sinapis arvensis, Sonchus oleraceus, Stellariamedia, Arctotheca calendula, Centaurea cyanus, Digitaria ischaemum,Fimbristylis miliacea, Galeopsis tetrahit, Galium aparine, Galiumspurium, Hirschfeldia incana, Limnocharis flava, Limnocharis erecta,Papaver rhoeas, Plantago lanceolata, Ranunculus acris, Carduus nutans,Carduus pycnocephalus, Centaurea soltitialis, Centaurea stoebe ssp.Micranthos, Cirsium arvense, Commelina diffusa, Echinochloacrus-pavonis, Soliva sessilis and Sphenoclea zeylanica, HPPD inhibitorresistant Amaranthus palmeri and Amaranthus rudis, PPO inhibitorresistant Acalypha australis, Amaranthus hybridus, Amaranthus palmeri,Amaranthus retroflexus, Amaranthus rudis, Ambrosia artemisifolia, Avenafatua, Conyza sumatrensis, Descurainia sophia, Euphorbia heterophyllaand Senecio vernalis, carotenoid biosynthesis inhibitor resistantHydrilla verticillata, Raphanus raphanistrum, Senecio vernalis andSisymbrium orientale, VLCFA inhibitor resistant Alopecurus myosuroides,Avena fatua and Echinochloa crus-galli.

The herbicidal compositions are suitable for combating/controllingcommon harmful plants in fields, where useful plants shall be planted(i.e. in crops). The inventive mixtures are generally suitable, such asfor burndown of undesired vegetation, in fields of the following crops:Grain crops, including e.g. cereals (small grain crops) such as wheat(Triticum aestivum) and wheat like crops such as durum (T. durum),einkorn (T. monococcum), emmer (T. dicoccon) and spelt (T. spelta), rye(Secale cereale), triticale (Tritiosecale), barley (Hordeum vulgare);maize (corn; Zea mays); Sorghum (e.g. Sorghum bicolour); rice (Oryzaspp. such as Oryza sativa and Oryza glaberrima); and sugar cane;

Legumes (Fabaceae), including e.g. soybeans (Glycine max.), peanuts(Arachis hypogaea and pulse crops such as peas including Pisum sativum,pigeon pea and cowpea, beans including broad beans (Vicia faba), Vignaspp., and Phaseolus spp. and lentils (Lens culinaris var.);brassicaceae, including e.g. canola (Brassica napus), oilseed rape (OSR,Brassica napus), cabbage (B. oleracea var.), mustard such as B. juncea,B. campestris, B. narinosa, B. nigra and B. tournefortii; and turnip(Brassica rapa var.);

other broadleaf crops including e.g. sunflower, cotton, flax, linseed,sugarbeet, potato and tomato;

TNV-crops (TNV: trees, nuts and vine) including e.g. grapes, Citrus,pomefruit, e.g. apple and pear, coffee, pistachio and oilpalm,stonefruit, e.g. peach, almond, walnut, olive, cherry, plum and apricot;

turf, pasture and rangeland; onion and garlic;

bulb ornamentals such as tulips and Narcissus;

conifers and deciduous trees such as Pinus, fir, oak, maple, dogwood,hawthorne, crabapple, and Rhamnus (buckthorn); and garden ornamentalssuch as roses, Petunia, marigold and snapdragon.

In one embodiment, the method for controlling undesired vegetation isapplied in cultivated rice, maize, pulse crops, cotton, canola, smallgrain cereals, soybeans, peanut, sugarcane, sunflower, plantation crops,tree crops, nuts or grapes. In another embodiment, the method is appliedin cultivated crops selected from glufosinate-tolerant crops.

The herbicidal are in particular suitable for burndown of undesiredvegetation in fields of the following crop plants: small grain cropssuch as wheat, barley, rye, triticale and durum, rice, maize (corn),sugarcane, Sorghum, soybean, pulse crops such as pea, bean and lentils,peanut, sunflower, sugarbeet, potato, cotton, Brassica crops, such asoilseed rape, canola, mustard, cabbage and turnip, turf, pasture,rangeland, grapes, pomefruit, such as apple and pear, stonefruit, suchas peach, almond, walnut, pecans, olive, cherry, plum and apricot,Citrus, coffee, pistachio, garden ornamentals, such as roses, Petunia,marigold, snap dragon, bulb ornamentals such as tulips and Narcissus,conifers and deciduous trees such as Pinus, fir, oak, maple, dogwood,hawthorne, crabapple and Rhamnus.

The herbicidal compositions are most suitable for burndown of undesiredvegetation in fields of the following crop plants: small grain cropssuch as wheat, barley, rye, triticale and durum, rice, maize, sugarcane,soybean, pulse crops such as pea, bean and lentils, peanut, sunflower,cotton, Brassica crops, such as oilseed rape, canola, turf, pasture,rangeland, grapes, stonefruit, such as peach, almond, walnut, pecans,olive, cherry, plum and apricot, Citrus and pistachio.

The invention also relates to plant propagation material comprising theherbicidal composition; and to a method for treating plant propagationmaterial comprising the step of treating plant propagation material withthe herbicidal composition.

In treatment of plant propagation materials such as seeds, e. g. bydusting, coating or drenching seed, amounts of glufosinate or saltthereof of from 0.1 to 1000 g, preferably from 1 to 1000 g, morepreferably from 1 to 100 g and most preferably from 5 to 100 g, per 100kilogram of plant propagation material (preferably seeds) are generallyrequired.

The treatment of plant propagation material comprises the step ofcontacting the plant propagation material with the herbicidalcomposition. The contacting may be carried out by all proceduresfamiliar to the person skilled in the art (seed dressing, seed coating,seed dusting, seed soaking, seed film coating, seed multilayer coating,seed encrusting, seed dripping and seed pelleting) based on theherbicidal compositions. Here, the herbicidal compositions can beapplied diluted or undiluted. The term “seed” comprises seed of alltypes, such as, for example, corns, seeds, fruits, tubers, seedlings andsimilar forms. Here, preferably, the term seed describes corns andseeds. The seed used can be seed of the useful plants mentioned above,but also the seed of transgenic plants or plants obtained by customarybreeding methods. Preferably, the term seed refers to a seed of amodified plant that is resistant against glufosinate.

Further objects of the invention are the use of the amine component forincreasing the herbicidal activity of liquid herbicidal compositionscomprising glufosinate, or a salt thereof, and a compound of formula(I); and a method for increasing the herbicidal activity of liquidherbicidal compositions comprising glufosinate or a salt thereof, and acompound of formula (I) comprising the step of contacting the liquidherbicidal composition with the amine component. The term “increasingthe herbicidal activity” refers to an enhanced controlling of undesiredvegetation as compared to a composition lacking the amine component. Theincreased controlling rate may typically be an enhancement of at least10%, preferably at least 25% as compared to a composition lacking theamine component. The contacting in the method of application usuallyrefers to admixing the amine component to the composition.

Advantages: the herbicidal compositions have an enhanced biologicaleffect on undesired vegetation as compared to liquid glufosinateformulations that contain a compound of formula (I) but not containingthe amine component. Another advantage is the reduced damage of certaincrop plants by the herbicidal composition, and a defoliation effect onother crop plants. Further advantages are a higher loading withglufosinate, lower application rates, and higher maximum concentrationswith compounds of formula (I).

The following examples illustrate the invention.

Ingredients:

Pesticide A: ammonium salt of glufosinateAdjuvant A: aqueous solution of alkylpolyglycosides, based onC₈-C₁₉-alcoholAdditive A: sodium laurylethersulfate containing two molecules ofpolymerized ethylene oxide, 70 wt % in water

EXAMPLE-1: PREPARATION OF HERBICIDAL COMPOSITIONS AND COMPARATIVECOMPOSITIONS

Four compositions according to the invention A1 to A4, as well as fourcomparative compositions AC1 to AC4 were prepared by mixing theingredients at the concentrations as provided in Tables A and B.

TABLE A Ingredients of compositions A1, A2, A3 and A4 in [g/l].Ingredient [g/l] A1 A2 A3 A4 Pesticide A 280 280 280 280 Additive A 222222 222 222 Adjuvant A — — — — Propylene glycol  46  46  46  46monomethyl ether Dipropylene glycol 116 116 116 116 Triethanolamine 176— — — Ethanolamine — 176 — — Diglycolamine — — 176 — Cholin chloride — —— 176 Water to 1 to 1 to 1 to 1 liter liter liter liter

TABLE B Ingredients of compositions AC1, AC2, AC3, and AC4 in [g/l].Ingredient [g/l] AC1 AC2 AC3 AC4 Pesticide A 280 280 280 280 Additive A222 222 296.4 222 Adjuvant A — 123 123 — Propylene glycol 46 46 46 46monomethyl ether Dipropylene glycol 116 116 116 116 Hexadecyltrimethyl176 — — — ammonium chloride Ethanolamine — — — — Diglycolamine — — — —Cholin chloride — — — — Water to 1 liter to 1 liter to 1 liter to 1liter

EXAMPLE-2: BIOLOGICAL TESTING ON CROP PLANTS

The compositions A1 to A4, and AC1 to AC4 as prepared in Example-1 weretested for their biological effect on the crops spring barley, Hordeumvulgare var. Adonis, and soybean, Glycine max var. Sultana. To this end,spring barley was grown to growth stage of 12/13 according to the BBCHscale. Soybean plants were grown to growth stages 14/15 according to theBBCH scale. Directly before application the plants were watered asneeded. Application of the herbicidal compositions was carried out in aspraying chamber. The herbicidal compositions were diluted with waterand applied in a rate of 200 liters/hectare. The amount of Pesticide Aapplied is listed in Tables C, C, E and F. After application the plantremained for 30 minutes minimum in a drying tunnel (air flow volume 3000m³/h) to get the surface of the plants complete dry before putting themin the greenhouse. The herbicidal activity was evaluated 7 and 20 daysafter treatment by awarding scores to the treated plants in comparisonto the untreated control plants (Tables C, D, E and F). The evaluationscale ranges from 0% go 100% activity. 100% activity means the completedeath of at least those parts of the plant that are above ground.Conversely, 0% activity means that there were no differences betweentreated and untreated plants. Experiments that were carried out on thesame days at the same time have the same letter in brackets in Tables C,D, E and F.

TABLE C control of spring barley with inventive compositions A1, A2, A3,and A4. The letter in brackets behind the composition name indicates atesting series from which the respective data were obtained. DAT is daysafter treatment; GS is growth stage according to BBCH scale. ApplicationControl of Control of rate Barley [%], Barley [%], [grams a.i./ GS12/13, GS 12/13, Composition hectare] 7 DAT 20 DAT A1(b) 300 58 63 A2(b)300 40 45 A3(b) 300 53 60 A4(c) 300 38 45

TABLE D control of spring barley with comparative compositions AC1, AC2,AC3, and AC4. The letter in brackets behind the composition nameindicates a testing series from which the respective data were obtained.DAT is days after treatment; GS is growth stage according to BBCH scale.Application Control of Control of rate Barley [%], Barley [%], [gramsa.i./ GS 12/13, GS 12/13, Composition hectare] 7 DAT 20 DAT AC1(a) 30035 25 AC2(b) 300 28 40 AC3(d) 300 50 38 AC4(b) 300 33 40

TABLE E control of soybean plants with inventive compositions A1, A2,A3, and A4. The letter in brackets behind the composition name indicatesthe testing series from which the respective data were obtained. DAT isdays after treatment; GS is growth stage according to BBCH scale.Application Control of Control of rate Soybean [%], Soybean [%], [gramsa.i./ GS 14/15, GS 14/15, Composition hectare] 7 DAT 20 DAT A1(b) 150 8075 A2(b) 150 80 78 A3(b) 150 85 83 A4(c) 150 88 73

TABLE F control of soybean plants with comparative compositions AC1,AC2, AC3, and AC4. The letter in brackets behind the composition nameindicates the testing series from which the respective data wereobtained. DAT is days after treatment; GS is growth stage according toBBCH scale. Application Control of Control of rate Soybean [%], Soybean[%], [grams a.i./ GS 14/15, GS 14/15, Composition hectare] 7 DAT 20 DATAC1(a) 150 58 15 AC2(b) 150 60 74 AC3(d) 150 70 50 AC4(b) 150 33 45

EXAMPLE-3: BIOLOGICAL TESTING ON ECHINACEA CRUS-GALLI

The compositions A1 to A4, and AC1 to AC4 as prepared in Example-1 weretested for their biological effect on the Echinacea crus-galli. To thisend, weeds were grown to growth stage of 16/18 according to the BBCHscale. Directly before application the plants were watered as needed.Application of the herbicidal compositions was carried out in a sprayingchamber. The herbicidal compositions were diluted with water and appliedin a rate of 200 liters/hectare. The amount of Pesticide A applied islisted in Tables G, and H. After application the plant remained for 30minutes minimum in a drying tunnel (air flow volume 3000 m³/h) to getthe surface of the plants complete dry before putting them in thegreenhouse. The herbicidal activity was evaluated 7 and 20 days aftertreatment by awarding scores to the treated plants in comparison to theuntreated control plants (Tables G, and H). The evaluation scale rangesfrom 0% go 100% activity. 100% activity means the complete death of atleast those parts of the plant that are above ground. Conversely, 0%activity means that there were no differences between treated anduntreated plants. Experiments that were carried out on the same days atthe same time have the same letter in brackets in Tables G, and H

TABLE G control of Echinacea crus-galli with inventive compositions A1,A2, A3, and A4. The letter in brackets behind the composition nameindicates a testing series from which the respective data were obtained.DAT is days after treatment; GS is growth stage according to BBCH scale.Application Control of Control of rate E.crus-galli [%], E.crus-galli[%], [grams a.i./ GS 16/18, GS 16/18, Composition hectare] 7 DAT 20 DATA1(b) 150 93 93 A2(b) 150 90 83 A3(b) 150 93 95 A4(c) 150 85 78

TABLE H control of Echinacea crus-galli with comparative compositionsAC1, AC2, AC3, and AC4. The letter in brackets behind the compositionname indicates a testing series from which the respective data wereobtained. DAT is days after treatment; GS is growth stage according toBBCH scale. Application Control of Control of rate E.crus-galli [%],E.crus-galli [%], [grams a.i./ GS 16/18, GS 16/18, Composition hectare]7 DAT 20 DAT AC1(a) 150 45 18 AC2(b) 150 88 78 AC3(d) 150 40 28 AC4(b)150 78 75

EXAMPLE-4: BIOLOGICAL TESTING ON GALIUM APARINE

The compositions A1 to A4, and AC1 to AC4 as prepared in Example-1 weretested for their biological effect on Galium aparine. To this end, weedswere grown to growth stage of 12/13 according to the BBCH scale.Directly before application the plants were watered as needed.Application of the herbicidal compositions was carried out in a sprayingchamber. The herbicidal compositions were diluted with water and appliedin a rate of 200 liters/hectare. The amount of Pesticide A applied islisted in Tables L, and M. After application the plant remained for 30minutes minimum in a drying tunnel (air flow volume 3000 m³/h) to getthe surface of the plants complete dry before putting them in thegreenhouse. The herbicidal activity was evaluated 7 and 20 days aftertreatment by awarding scores to the treated plants in comparison to theuntreated control plants (Tables L, and M). The evaluation scale rangesfrom 0% go 100% activity. 100% activity means the complete death of atleast those parts of the plant that are above ground. Conversely, 0%activity means that there were no differences between treated anduntreated plants. Experiments that were carried out on the same days atthe same time have the same letter in brackets in Tables L, and M.

TABLE L control of Galium aparine with inventive compositions A1, A2,A3, and A4. The letter in brackets behind the composition name indicatesa testing series from which the respective data were obtained. DAT isdays after treatment; GS is growth stage according to BBCH scale.Application Control of Control of rate G.aparine [%], G.aparine [%],[grams a.i./ GS 12/13, GS 12/13, Composition hectare] 7 DAT 20 DAT A1(b)150 83 63 A2(b) 150 75 53 A3(b) 150 90 80 A4(c) 150 65 55

TABLE H control of Galium aparine with comparative compositions AC1,AC2, AC3, and AC4. The letter in brackets behind the composition nameindicates a testing series from which the respective data were obtained.DAT is days after treatment; GS is growth stage according to BBCH scale.Application Control of Control of rate G.aparine [%], G.aparine [%],[grams a.i./ GS 12/13, GS 12/13, Composition hectare] 7 DAT 20 DATAC1(a) 150 68 43 AC2(b) 150 80 53 AC3(d) 150 85 68 AC4(b) 150 48 18

EXAMPLE-5: BIOLOGICAL TESTING ON ABUTILON THEOPHRASTI

The compositions A1 to A4, and AC1 to AC4 as prepared in Example-1 weretested for their biological effect on Abutilon theophrasti. To this end,weeds were grown to growth stage of 14/15 according to the BBCH scale.Directly before application the plants were watered as needed.Application of the herbicidal compositions was carried out in a sprayingchamber. The herbicidal compositions were diluted with water and appliedin a rate of 200 liters/hectare. The amount of Pesticide A applied islisted in Tables N, and O. After application the plant remained for 30minutes minimum in a drying tunnel (air flow volume 3000 m³/h) to getthe surface of the plants complete dry before putting them in thegreenhouse. The herbicidal activity was evaluated 7 and 20 days aftertreatment by awarding scores to the treated plants in comparison to theuntreated control plants (Tables N, and O). The evaluation scale rangesfrom 0% go 100% activity. 100% activity means the complete death of atleast those parts of the plant that are above ground. Conversely, 0%activity means that there were no differences between treated anduntreated plants. Experiments that were carried out on the same days atthe same time have the same letter in brackets in Tables N, and O.

TABLE N control of Abutilon theophrasti with inventive compositions A1,A2, A3, and A4. The letter in brackets behind the composition nameindicates a testing series from which the respective data were obtained.DAT is days after treatment; GS is growth stage according to BBCH scale.Application Control of A.theo- Control of A.theo- rate phrasti [%],phrasti [%], [grams a.i./ GS 14/15, GS 14/15, Composition hectare] 7 DAT20 DAT A1(b) 300 97 98 A2(b) 300 97 98 A3(b) 300 98 98 A4(c) 300 95 98

TABLE O control of Abutilon theophrasti with comparative compositionsAC1, AC2, AC3, and AC4. The letter in brackets behind the compositionname indicates a testing series from which the respective data wereobtained. DAT is days after treatment; GS is growth stage according toBBCH scale. Application Control of A.theo- Control of A.theo- ratephrasti [%], phrasti [%], [grams a.i./ GS 14/15, GS 14/15, Compositionhectare] 7 DAT 20 DAT AC1(a) 300 88 85 AC2(b) 300 98 98 AC3(d) 300 65 63AC4(b) 300 97 97

EXAMPLE-6: BIOLOGICAL TESTING ON SETARIA MACROSTACHYA

The compositions A1 to A4, and AC1 to AC4 as prepared in Example-1 weretested for their biological effect on Setaria macrostachya. To this end,weeds were grown to growth stage of 12/13 according to the BBCH scale.Directly before application the plants were watered as needed.Application of the herbicidal compositions was carried out in a sprayingchamber. The herbicidal compositions were diluted with water and appliedin a rate of 200 liters/hectare. The amount of Pesticide A applied islisted in Tables P, and Q. After application the plant remained for 30minutes minimum in a drying tunnel (air flow volume 3000 m³/h) to getthe surface of the plants complete dry before putting them in thegreenhouse. The herbicidal activity was evaluated 7 and 20 days aftertreatment by awarding scores to the treated plants in comparison to theuntreated control plants (Tables P, and Q). The evaluation scale rangesfrom 0% go 100% activity. 100% activity means the complete death of atleast those parts of the plant that are above ground. Conversely, 0%activity means that there were no differences between treated anduntreated plants. Experiments that were carried out on the same days atthe same time have the same letter in brackets in Tables P, and Q.

TABLE P control of Setaria macrostachya with inventive compositions A1,A2, A3, and A4. The letter in brackets behind the composition nameindicates a testing series from which the respective data were obtained.DAT is days after treatment; GS is growth stage according to BBCH scale.Application Control of Setaria Control of Setaria rate macrostachya [%],macrostachya [%], [grams a.i./ GS 12/13, GS 12/13, Composition hectare]7 DAT 20 DAT A1(b) 75 95 98 A2(b) 75 93 98 A3(b) 75 95 98 A4(c) 75 93 90

TABLE Q control of Setaria macrostachya with comparative compositionsAC1, AC2, AC3, and AC4. The letter in brackets behind the compositionname indicates a testing series from which the respective data wereobtained. DAT is days after treatment; GS is growth stage according toBBCH scale. Application Control of Setaria Control of Setaria ratemacrostachya [%], macrostachya [%], [grams a.i./ GS 12/13, GS 12/13,Composition hectare] 7 DAT 20 DAT AC1(a) 75 85 78 AC2(b) 75 95 98 AC3(d)75 90 93 AC4(b) 75 — —

EXAMPLE-7: BIOLOGICAL TESTING ON BASSIA SCOPARIA

The compositions A1 to A4, and AC1 to AC4 as prepared in Example-1 weretested for their biological effect on Bassia scoparia. To this end,weeds were grown to growth stage of 14/15 according to the BBCH scale.Directly before application the plants were watered as needed.Application of the herbicidal compositions was carried out in a sprayingchamber. The herbicidal compositions were diluted with water and appliedin a rate of 200 liters/hectare. The amount of Pesticide A applied islisted in Tables R, and S. After application the plant remained for 30minutes minimum in a drying tunnel (air flow volume 3000 m³/h) to getthe surface of the plants complete dry before putting them in thegreenhouse. The herbicidal activity was evaluated 7 and 20 days aftertreatment by awarding scores to the treated plants in comparison to theuntreated control plants (Tables R, and S). The evaluation scale rangesfrom 0% go 100% activity. 100% activity means the complete death of atleast those parts of the plant that are above ground. Conversely, 0%activity means that there were no differences between treated anduntreated plants. Experiments that were carried out on the same days atthe same time have the same letter in brackets in Tables R, and S.

TABLE P control of Bassia scoparia with inventive compositions A1, A2,A3, and A4. The letter in brackets behind the composition name indicatesa testing series from which the respective data were obtained DAT isdays after treatment; GS is growth stage according to BBCH scale.Application Control of Bassia Control of Bassia rate scoparia [%],scoparia [%], [grams a.i./ GS 14/15, GS 14/15, Composition hectare] 7DAT 20 DAT A1(b) 150 75 87 A2(b) 150 75 87 A3(b) 150 78 79 A4(c) 150 9094

TABLE Q control of Bassia scoparia with comparative compositions AC1,AC2, AC3, and AC4. The letter in brackets behind the composition nameindicates a testing series from which the respective data were obtained.DAT is days after treatment; GS is growth stage according to BBCH scale.Application Control of Bassia Control of Bassia rate scoparia [%],scoparia [%], [grams a.i./ GS 14/15, GS 14/15, Composition hectare] 7DAT 20 DAT AC1(a) 150 25 30 AC2(b) 150 83 98 AC3(d) 150 70 79 AC4(b) 15075 20

1. A liquid herbicidal composition comprising a) glufosinate, or a saltthereof; b) an amine component selected from primary, secondary,tertiary amines, and ammonium salts thereof, and quaternary ammoniumsalts; wherein the molecular weight of the primary, secondary ortertiary amines, of the ammonium cation in the ammonium salts, or of thequaternary ammonium cation in the quaternary ammonium salts is from 32to 200 g/mol; c) a compound of formula (I)[R-(A)_(x)-OSO₃ ⁻]-M⁺  (I); wherein R is C₁₀-C₁₆-alkyl, C₁₀-C₁₆-alkenyl,or C₁₀-C₁₆-alkynyl; each A is independently a group

wherein R^(A), R^(B), R^(C), and R^(D) are independently H, CH₃, orCH₂CH₃ with the proviso that the sum of C-atoms of R^(A), R^(B), R^(C),and R^(D) is up to 2; M⁺ is a monovalent cation; and the index x is anumber from 1 to 10; wherein the amine component is an amine selectedfrom ethanolamine, diglycolamine, 1-aminopropan-2-ol,2-dimethylaminoethanol, or an ammonium salt thereof, or a salt oftrishydroxyethylmethyl ammonium.
 2. The composition according to claim1, wherein the index x is from 1 to
 3. 3. The composition according toclaim 1, wherein R^(A), R^(B), R^(C), and R^(D) are H.
 4. Thecomposition according to claim 1, wherein M⁺ is Na⁺.
 5. The compositionaccording to claim 1, wherein the pH is from 6 to
 10. 6. The compositionaccording to claim 1, wherein the amine component is a chloride,sulfate, sulfonate, or methylsulfonate salt of a primary, secondary, ortertiary ammonium cation.
 7. The composition according to claim 1,wherein the component a) is the ammonium salt of glufosinate.
 8. Thecomposition according to claim 1, comprising a) 5 to 50 wt % ofglufosinate, (L)-glufosinate, or a salt thereof; b) 5 to 50 wt % of theamine component; c) 5 to 60 wt % of the compound of formula (I).
 9. Thecomposition according to claim 1, wherein the amine component isethanolamine.
 10. The composition according to claim 1 containing asecond agrochemical active ingredient selected from herbicides ofclasses b1) to b15) and safeners C).
 11. A method for increasing anherbicidal activity of a liquid herbicidal composition comprising a)glufosinate or a salt thereof and b) a compound of formula (I)comprising contacting the liquid herbicidal composition with c) an aminecomponent as defined in claim
 1. 12. A method for treating plantpropagation material comprising the treating plant propagation materialwith the herbicidal composition as defined in claim 1.